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",2DGEWOOD AR'.SENAL SPECiAL PUBLICATION

EASP 100-4

I PHOTOCHEMISTRY OF HIETEROCYCLIC COMPOUNDS

A Literature Survey

H by

Edward J. Poziomek

September 1966

I '•ihis document is subject to special export controls and eachc-ansmittal to foreign governments or foreign nationals mayý.n- made only with prior approval of the Conmmanding Offi-

•r, US Army Edgewood Arsenal, ATTN: SMUEA-TSTI-T,,dzgewood Arsenal, Maryland 21010.

Task IC622401AI0204

Physical Research La.boratoryResearch Laboratories

US ARMY EDGEWOOD ARSENALEDGEWOOD ARSENAL, MARYLAND 21010

It _

FOREWORD

Thas work was conducted under the Mutual Educational and Cultural

Exchange Act of 1961, Public Law 87-256. It is being published under TaskI 1Ch22401A10204, Detecti~n and Warning Investigations (U).

ThA survey was made during September l9•5~, while the author was

on a leave of absence.

Reproduction of this document in whole or in part is prohibitedexcept with permission of the Commanding Offi'-.r, US Army Edgewood Arsenal,ATTN: SMUEA-TSTI-T, Edgewood Araenal, Maryland 21010; however. DDCis authorized to reproduce the document for United States Government purposes.

A

2

* 2

I--

DIGEST

The literature on the photochemistry of heterocclic corpowndsý%ao surveyed with a particular interest in pyridine chemistry.

This listing of relerences was comp':ed as a result of wearchingvolumes 41 to 61 of Chemical Abstracts under the headings light, photochem-istry, and pyridine. References to earlier work may be found in The Actionof Ultraviolet Rays by C. Ellis and A. A. Wells (Reinhold Publishing Corp.,New York, New York, 1941).

A complete survey of the photochemistry of heterocyclic compoundsrequires searching under each heterocyclic -ring heading, This presents achallenge that could not be met. Additional references may be found, however,in Priparative Organilche Photocheinie by A. Schlnberg (Springer-Verlag,Berlin-Wilrneradorf (West), Germkny, 1958] and in the Advances in Photochern-istry series (Interscience Publishers, Inc., New York, New York, 1963).

3

CON TEN TS

- i-

1. INTRODUCTION ......... . . ............................. 7

-• 111, KEYWORK INDEX ................................. . . . . 27

"•=-=DISTRIBUTION LIST ........... ............................. 3 1 E -

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THE PHOTOCT !'.Z..TR r OF HETEROCYCtLiC COMPOUNDSA Literature Survey

1 . INTRODUCTION,

The US Army is interested in photochemistry for use in the iields

of detection, stability of reagents, and synihe•:-, .'o a few. This list-

ing of references provides ;, convenient source of citations for researchersfaced with prcolams in photochemistry. References are listed alphabetically

by author, and keywords are listed beside each reference as well as in analphabetical index. The title following the author's name is either a para-

phrased Journal article title or, in instances where the article was not en-

tirely about the photochemistry of heterocyclics, an indication of that part

of heterocyclic photochemistry with which the article dealt.

11. REFERENCE LIST.

Rhodoputn 1. Adams, R. G. Flash Photolysis ef Rhodopuin in Solution.Dissertation Abstr. 20, 2782 (1960). [Chem. Abstr. 54,1 1662b]4

Nicotinamide 2. Alechinsky, A. and Reuse, J. NiLotinamide in

Histidine Relation to Hiutidine Irradiation by Light. Compt. Rend.Soc. Biol. 140, 1224 (1946). [Chem. Abstr. 42, 626b.]

Diazirine 3. Arnrich, M. J., and Bell, J. A. Photolsomerization of

Diazirine. J. Am. Chem. Soc. 83, 292 (1964).

Methylene blue 4. Angelescu, E., and Cornea, F. Methylene Blue Reaction

Thiourea Witih Thiourea in Light. Analele Univ. "C. I. Parhon"

Ser. Stiiut. Nat. 9, No. 26, 123 (1960). [Chem. Abstr.59, 1452c.]

Pyridones 5. Ayer, W. A., Hayatsu, R., de Mayo, P., Reid, S. T.,

and Stothers, J. B. Photodimers of Pyridoqes. Tetra-hedror Letters,No. 18, 648 (1961).

Ferrocyanide- 6. Balzani, V., Caraesiti, V., and Loce, R. S. Substitu-

2, 2'-bipyridine tion Reactions in the Ferrocyanide-2, 2'-bipyridine, and

Ferrocyanide- Ferrocyardde-1. lO-phenanthroline Systems. Ann. Chirn.

1, 10-phenan- (Rome) 54, 103 (1964). (Chein. Abstr. 61, 10220h.]throline

11 -,I I I I I I II7I

V-BL, AFY4SA 7. i D lzaniL4 , V. , ,.arasaklk, V~. andl( PAuthi, L., Lightand o-phenan- Induced Decomposition of Tetracyanoferrate Con-plexspnthroline tetra- of Bipyridine and o-Phenanthroline, Ann. Chimn. (Rome)Cyanoferrate 54, 251 (1964. jChem. Abstr. 61, 5120f.1

2- . barnaoex, ', , - i igheoti, L4 ., 4-- ,,l I -

Action on Yeast and Light, Boll. Soc ltai. Biol. Sper.Yeast 30, 461 (,954). [Cheni. Ab.tr. 49, 1872c.1

Pnotography 9. Belgian Patent 557, 657 (to Kodak So--.. Anon. }. Photo-Pyridine graphic Emulsions Supersenaitized by -yrid-ine or Pico-bensitizer line. Juna 15, 1957. [Chem. Abstr. 54. 1J a..Picoli nesaensitizer

13enzotria- 10. Belgian Patent 628, 131 (to Societa Generale per- zoles 1'Industria Meneraria e Chimica). Light Stabilizer,

Benzotriazole Hydroxy Derivatives. August 7, 1963.[Chem, Abstr. 60. 14688b. I

* Malononitrile 1. Belgian Patent 633, 103. Heterocyclic Compounds Resia-derivatives tant to Light. Phenyl- (2-thienylmethylene)malononitrile.

hPenyl-(Z-thi- October -1, 1963. 'Chem. Abstr. 61. 8279i.]enylm-ethylene)-

Methyl and 12. Bencze, W. L., Burckhardt. C. A., and Yost, IV, L.

phenyl pyridyl Photochemical Preparation, Rearrangement, and Dehy-glycols dration of Symmetrical Methyl and Phernyl PyrirAyl Gly-Pyridyl glycols cola. J. Org. Chem. 27, 2865 (1962).Ketones"Pyridyl ketone-

Dihydropyri- 13. Berson, J, A., and Brown, E. Irradiation of Dihydro-dine pyridinee. J. Am. Chem. Soc. 77, 450 (1955).

.3- .ndopa...ti. 14 -.rth.... A .. and Anc r. eux, G. J-Iri.u..acetic Acidacid From Tryptophan by Action of Light. Conipt. Rend.Tryptophan 206, 699 (1938). [Chem. Abstr. 32, 41b1 6.1

-i 1

3 -Indoleacetic 1S. Berthelot. A., Arnoureux G. and Debe.rqJib e, 5.Acid .I-Indoleacetic Acid From Tryptophan by Action of Ultra-

Tryptaph~n violet Light, Compt. Rend. Soc. Biol. 131, 1234 (1939).

tChem. Abatre 3., 4...l

Pyrimidines 16r Oeukers. R. , and Berends, W. Effect of Paramagnetict

•. . "t, . t• %,J,,- Vt..S. . s Ot !o0,y I F ,,rim idltie Df-riv-

atives by Ultraviolet Radiation. Diochim. Biophyr.

Acta 38., 573 (1960). [Chem. Abatr. 54, i6499d.

Pyrethrin 17. llackith, R. E. Pyrethrin Deconmposition by Light.

Sci. Food Age, 3. 219 (19S2). [Chem. Abntr. 47,

350geh. ]

Rhodopoin 18, S Mius, A. F. Rhodopsin Transforrnation to Yellow

Lipida in Light. 3. Biol. Cheni. 17.2, 165 (194A),

tChem. Abstr. 42, 3002f,] 3Thiopyronine 19. Boehme, H. . and Wacker, A. Mutageniv Activity of

Methylene blue Thiopyronine and Methylene Blue in Combination WithVisible Light. Biochem. Biophys. Res- Comnm't.n. 12,I137 (1963). [Chern. kbstr. bO, II095f.]

Carbazole Z0. Bowen, E. J., and Eland, J. H. D. Carbazole Forma-MIEnhnvyam~n@ tion From Diphenviamine in Presence of Light. Proc.

Chem. Soc, . Io (1963). jChem. Abetr. 59. 9443a.

ITndoieacetlc 21. Brainer. I . I-Indoleacetic Acid Decomposition. Nator-

acid wiesenschaften 40, 23 (1953). [Chem. Abstr. 47, 3I 2000g. 1

..lndolpaceiic 22. Brauner, L. 3-IndoleaceLic Acid Decoripoeition byacid Light. 7. Botan. 41, 21 (1953). [Chem. Abstr, 48,

5Z9ga.'

3.lndoleacetic 23. Frauner, L. 3-Indoleacetic Acid Decompositior. by

Sacid Light. Z2 Botan. 4Z, 83 (i954)i. '.b.. . .. 486842h. I

Visual pig- 24. Bridges, C. D_ B. t lash F'hotolysia of Vittlml Figmoritas.

metit a I. Piginents Present it, F-og-Pio-dopsin Soutions After

Rhodupain Flash Irradiati•t.. ljioc|e, , J1. 76i, W461 (1 K1) -en. IT,.

-Absr, S , 2290h

Z, d. d , C. D.. Production of Thermally Stable

-Thve; Ytazensitive P- gments in Flash Irradiated Solutions of

_ __• io • o~g Rhiodopsin. Biochen•. J. 79, 135 (1961). [Chem.

A c . 2 2 3 -

OL P, 0. Pjtocheni~cal Rearrangement of Quino-Ii ne-NT-oxide. Acta Chem. Scand. 17, 1461 (1963).

27. .uchardt, 0. Stz ucture of the Photodimers of Carbo-, ! - styril and N-Methylcarbostyril. Acta Chem. Scand. 18,

" ..... "1389 (1.964).

Quinolt... -- N- 28. BTuchardt, 0., Becher, J. , and Lohse, C. Photorear-

oxi~de rangernent of Methyl Substituted Quinoline-N-oxides.Acta Chem. Scand. 19., 1120 (1965).

Pvridirý 29. Cantieni, R. Effect of Light on Pyridine Mixtures With

Sugars, Monohydric Alcohols and Acetone. Helv. Chim.Acta 18, 1420 (1935). [Chem. Abetr. 30, 16623.]

Dipyridyll 30. Carassiti, V., Condorelli, G., and Costanzo, L. L.

Silver C 'pyri- Photochemistry of Silver Dipyridyls. Ann. Chim.

dyls (Rome) 54, 303 (1964). [Chem. Abstr. 61, 5120f.]

DPN (d ,hos- 31. Carter, C. E. Effect of Light on Adenosine Triphosphate

phopyric ine and Diphosphopyridine Nucleotide. J. Am. Chem. Soc.

rn ulCI e0 ti '4 72, 1835 (1950).

ATP-l (ac:no-

-.A Az, 5, 7 32ý Chapman, 0. L., and Hoganson, E. D. Photoisomeri-trimne• .iy ~ zatior of 1-Aza-3, 5, 7-trimethylcyclohepta-4, 6-dien-

-4 6- 2-one. J. Am. Chem. Soc. 86, 498 (1964).

33. Conrad, W. E. Uri.zil Decomposition by Light. Radia-tion Res. 1, 523 (1954). [Chem. Abstr. 49, 4412e.]

34. Corey, E. J., and Streith, J. Internal Photoaddition

"I - M e .11Reactionv of 2-Pyrone and N-Methyl-Z-pyridone. J. Am.pyr~idor• Chem. Soc. 86, 950 (1964).

'i0

~• .H., ', G., and elwoiod, P. W. Effect of Light-lisulfide. J1. Az.-,. Cher. Soc. 70"

,. Action of Light on Aqueous 5blutions of-'n pyrv- trar:!-.Pyridine Derivatives of Iridium and Rhodium.

dir:_ • ;f yl- omnpt. Rend. 240, 2468 (1955)..

i -id Ia -nd 37. Del'pine, M. Effect of Light on Aqueous Solutions ofrhoaii, rn pyri- cit-Dipyridine-tetrachloro Derivatives of Iridium anddine triva- Rhodiurn. Cornpt. Rend. 242, 27 (1956). [Chem. Abstr.tivej 50, 9883i.]

Qtini 5hydro- 38. Delperdange, G. R. Quinine Hydrochloride SensitivitychIo' ..... to Light, Effects of -Crystal Form. Rev. Paludisme

Me"d. Trop. 6. 103 (1948). [Chem. Abstr. 43, 2839c.]

Fryp't.ahan 39. Deschreider, A. R., and Renard, M. TryptophanDecomposition by Light. Bull. Inst. Agron. Sta. Rech.Gembloux 23, 269 (1955). [Chem. Abstr. 50., 3904f.]

Trypt ;Jihan. 40. Descbreider. A. R.. and Renard, M. TryptophanIrradiated by Light. Spectrum of. Bull. Inst. Agron.Sta. Rech. Gembloux 23, 151 (1955). [Chem. Abstr.490 15482e.]

4-. Dcssauer, R., and Pari5, J. P. Photochromism ofM•,I• t ne b7.1e 2- (2', 3?.-Dinitrobenzyl)pyridine, Xanthylidimeanthrone.Xanth. i•idine- Spirans, and Methylene Blue. Advances in Photochemnis-anthr- try. Vol 1, p 275. Interscience Publi.lhera, Inc.,

Sirdtz .oz yl- New York, New York. - 1963.

42. Doep/fere, W., and Geletti, A. The Forrrmation of Sern-

5-k-cyd oxytry-- tonin From 5-I-ydrozytryptophan With Ultraviolet Irradia-,opi,,•w tion. Experientia 14, 376 (1958). [Chem. Abstr. 53,

14015e. I

Pyove 'line 43. Elliott, R. P. Pyoverdine Decomposition by Light.Peud Lrnonads Appl. Microbiol. 6, 2,41 (1958). [Chern. Abstr. 52_.

18654d. ]

IL

Photrchomis- 44. ElIhs, C., and Wells, A. A. The Chemical Action ofry Ultraviolet Rays. Rsinhold Publishing Corp. New York,

Hettrocvclics New York. 1941.(early work)

PVridine 4S. Faigl, F., and Anger, V. Photopuridine Reaction.J. Prakt. Chem. 139, 180 (1934). .Chem. Abstr. 28,23345.1

Pyridine 4(: Fialkovskaya, 0. V., and Terenin, A. N. PyridineAdsorbed on Silica Gels Irradiated by Light. Izv. Akad.Nauk SSSR Otd. Khim. Nauk, 226 (1951). [Chem.Abstr. 45, 9374g.]

Histamine 47. Flemming, K. Mechanism of Histamine Formation inHistidine Histidine Solution Irradiated With Ultraviolet L.ight.

Arch. Exptl. Pathol. Pharmakol. 236, 27 (1959).[Chem. Abetr. 53, 10350d.]

T riazinea 48. Freeman, H. C., and Le Fevre, R. J. W. 1, 3-Diphenyl-triazine Decomposition h;,- Light. J. Chem. Soc., 2932(1952). [Chem. Abstr. 46, 10903e.]

Dicirine 49. Frey, H. M., and Stevens, 1. D. R. Phutolysis ofDiazirine. Proc. Chem. Soc. 79, (1962).

PyriJine 50. Freytag, H. Action of Ultraviolet Light on PyridineDer-vatives. Chkam. S ;r. 695 32 (1930). [Ch'-m.Abstr. 30, 29666. 1

Pyridine 51. Freytag, H. Photochenr..stry of Pyridine arnd Its Deriva-Pyridines tives, Phot. Korr. 73, 17, 37, 57 (1937). [Chem.

Abstr. 32., '8393.] I

Pyridine 52. I'reytag, H. Pyridine Decomposition by Light (.AnalyticalPrinci71es). Z. Anal. Chern. 152, 86 (, Y6). [Cherr.Absti. 51, 3372b."

Tiata,ninp -1 53 Fuiiwp a, T , Taaanu,_ T 1., Morokurna, T., and

Histidine Yarnada, M. Dezonvosution by Light of Histamnine,Imidazole P'stidine and Imidazele Derivatives. Nagasaki IgakkaiZasshi 24, 726 (1954). [Chemn. Abstr. 49, 2538i.]

Riboflavine 54. Fukamachi, C., and Sakurai, Y. Photolytic Formation Iof 6, 7-Dimethylflavin-9-acetic Acid From Riboflavine.Shokuryo Kenkyusho Kenkyu HokokuNo. 10, 207 (1955).[Chem. Abstr. 53, 14111c.]

Thiophenes 55. German Patent 955, 379 (to Kalle and Co. Akt. -Gee.).

Light-Sensitive Material for Reproduction. (NitratedThiophene Derivatives). January 3, 1957. [Chem.Abstr. 54, 12840f.]

Acridine 56. Giurgea, M., Mihai, G., Topa, V., and Musa, M.Acridan Photochemical Reactions in Solutions of Acridine aiLd

Acridan. J. Chim. Phys. 61, 619 (1964). (Chem."Abstr. 61, 5483h.]

Pyrethrum 57. Glynne Jones, G. D. Pyrethrum Decomposition byLight. Ann. Appl. Biol. 48, 352 (1960). [Chem.Abstr. 5_5, 2145h.]

Ethylene oxide 58. Gomer, R., and Noyes, W. A., Jr. PhotochemicalDecomposition of Ethylene Oxide. J. Am. Chem. Soc.72, 101 (1950).

Indole 59. Hantsu, S. Photolysis of Indole. Nagasaki Igakkai

Zasshi 35, 65 (1960). [Chem. Abstr. 54, 18035b.]

Rhodopsin 60. Hara, R., and Takagi, M. Effect of Illumination on theElectrical Conductance of Rhodopsin at Low Tempera-

•=• ~tut-e. Dobutaugaku Zaeshi 69_, 255 (1960). [Chem.

Abstr. 55, 20030r.]

Nitrobenzyl- 61. Hardwick, R,., and Mosher, H. 3. - 2 , 4-Dinitrobenzyl-pyridines pyridine Reactions in Presence of Light. J. Chem.

Phys. 36, 1402 (1962), [Chem. Abstr. 57., 42Z2b.

2-Picoline- 62. Hata, N. 2-Picoline-N-oxide Decompo••ition by Light.IV -oxide Bull. Chein, Zoc. Japan 34., 1440 (1961). [Chern, Abstr.

56, 4286b.]

3-Picoline- 63, Hata, N. 3-Picoline-N -oxide Decornpositiorn b', Light.N-oxide Bull. Chera. Soc. Japan 34, 1.444 (1961). [Che-n.

Abstt. 5b, 4286e.] -

131 .

-iPyridine-N- 64. Hata, N., and Tanaka, 1. Pyridine-N-oxcde Derivativesoxide Irradiated by Light. J. Chem. Phys. 36, 2076 (1962).

(Chem. Abatr. 57, 5888f.]

Formaxano 65. -lausser, 1., Jerchel, D., and Kuhn, R. Rearrangementof Formazans by Light. Chem. Ber. 82, 515 (1949).

[Chem. Abt. o 44, 3927h.]

Tetraoliunm 66. Hausser, K. H. Decomposition of Triphenyltetrazoliumcompounds Chloride and Triphenylformazan. NaturwissenschaftenTriphanyltetra- 36, 313 (1949). [Chern. Abstr. 44._, 5713e.]

zolium chlorideFormaxans

Triphenylform-azan

Pyridylacrylic 67. Henze, M. Attempted Polymerization of Pyridyl Acrylicacid Acid. Chem. Ber. 70B, 1273 (1937). [Chem. Abstr.

Riboflavine 68. Hioki, H., and Sakurai, Y. On the Inhibition of Ribo-flavine Photolyeis With Apple Juice. Bitamin (Kyoto) 8,380 (1955). [Chem. Abstr. 51, 18027abd.]

Riboflavine 69. Moki, H., and Sakurai, Y. On the Photolytic Formationof 6. 7-Dimethvlflavine- 9-acetic Acid From Riboflavine.

Bitamin (Kyoto) 7, 1014 (1954). [Chem. Abstr. 51,1 8026gi. I

Vitamin B 2 70. Hioki. H., and Sakurai, Y. Vitamin BZ Photolysis. V.Riboflavine The Photolytic Formation of 6, 7-Dimethylflavine-9-

acetic Acid Ester From Riboflavine. Bitamin (Kyoto)7, 939 (1954). [Chemn. Abstr. 51, 18026gi.]

Riboflavine 71. Hioki, H., and Sakurai, Y. Why Fructose Inhibits thePhotolysis of Riboflavine in Alkaline Solution. Bitamin(Kyoto) 9, 221 (1955). [Chem. Abstr. 51, 18027abd.)

Riboflavine 72. Holmstroon, B., and Oster, G. Riboflavine as an Elec-tron Donor in Photochemical Reactions. J. Am. Chem.Soc. 83, 1867 (1961). [Chem. Abstr. 55, 19429e.]

14

___________

Ferric salts 73. Ign&tieff, V. Effect of Light on Reduction of Ferric Ion[2, 2'-Bipyrid:ne by Citrate and 2, 2'-Bipyridine. J. Soc. Chemn. Ind. 56,

407 (1937). [Chem. Abstr. 32, 13769.]

Imidazole 74. Inoue, M., Takano, N., and Morokuma, T. ImidazoleAcetic Acid Decomposition by Light. Nagasaki IgakkaiZasshi 29, 549 (1954). [Chem. Abstr. 48, 13759b.]

Phenothiazine 75. Ippen, H. Effect of Light on Phenothiazine and Sulfona-Sulfonamide mide Derivatives. Proc. Intern. Congr. Photobiol., 3rd,

Copenhagen 1960, 509-514 (Pub. 1961). (German).[Chem. Abstr. 60, 6054e.]

Riboflavine 76. Ishiguro, I., Kato, Y., and Suguira, M. The Mechanismof Riboflavine Photolysis and Its Stability. Gifu YakkaDaigaku Kiyo 8, 49 (1958). [Chem. Abstr. 53., 10321i.]

4-Azidopyri- 77. Itai, T.. and Kamisja, S. 4-Azidopyridine Relateddine Compounds Cleavage by Light. Chem. Pharm. Bull.

(Tokyo) 9, 87 (1961). [Chem. Abstr. 55, 27338c.]

1, 2-Betziso- 78. Italian Patent 652, 828 (to Montecatini),. Stabilizer forthiazolin-3- Olefin Polymersi 1, Z-Benzisothiazolin-3- one-1, 1-

hone-l, l-di- dioxide. February 23, 1963. [Chem. Abstr. 60,0 -X oid e 9437h. j

Acridine 79. Ivanoff, Nira. Ac~ion vf Ultraviolet and y-Radiation on9-Methylacri- Solutions of Acridine. 111. Quantum Yield for the Reac-

Sdine tion of Acridine and 9-Methylacridine With Carbon Tetra-chloride. J. Chiun. Phys. 55, 7b8 (1958). [Chem.Abstr. 53, 19534h.]

Acidine 80. Ivanoff, Nina, and Walch, France. Action of UltravioletLight on Solutions of Acridine (Halogenated Solvents).J. Chim. Phys. 56, 574 (1959). [Chem. Abstr. 51,

161 12fi-

Tetrazolium 81. Jambor, B. Reactions of Tetrazolium Compounds incompounds the Presence of Light. Pharmazie 13. 277, 282, 411,

414 (1958). [Chem. Abstr. 53, 4264f.

15

- I I I I I I

Bensotria- 82. Japanese Patent 2176 (to O0 ka Seika Industry Co.,mole deriva- Ltd.). Light Stabilizer, 2-(2-Hydroxy-5-methyphenol)-tives benzotriasole. May 23, 1962. [Chem. Abstr. 60,

10890b. ]

H/droixypy- 83. Japanese Pateat 5647 (to Shin Fujisawa). Photosensitiverimidines Material (Hydroxypyrimidine Derivatives). June 29,

1959. (Chem. Abstr. 53, 21309f. I

Thymine 84. Johns, H. E., Rapaport, S. A., and Delbruwk, M.dimrers Photochemistry of Thymire Dimers. J. Mos. Biol. 4,Dinucleotides 104 (1962). [Chem. Abstr. 57, 2549e.I

4,4'-Bipyri- 85. Johnson, C. S., Jr., and Gutowsky, H. S. Decomposi-dine tion of Benzyl, Ethyl and Methyl Viologens and 4, 4'-Viologens Bipyridine. J. Chem. Phys. 39, 58 (1963). [Chem.

Abstr. 59, 2315c.]

Triazines 86. Jordan, L. S., Day, B. E., and Clerx, W. A. Photo-decomposition of Triazines. Weeds 12, 6 (1964).

[Chem. Abstr. 60, 1130 2 g.]

Pyrirmldines 87. Kalab, D. Application of Oscillographic Polarographyin Photochemistry. I. Pyrimidines. Chem. Zvesti 18,435 (1964), [Chem. Abstr. 61, 11515d.]

Quinoxalines 88. Kawai, S., Tanaka, S., and Ichikawa, K. Synthesis ofDihydroxy- 2, 3-Dimethyl-5, 8-dihydroxyquinoxaline and the Influencequinoxaline of Light Upon Catalytic Hydrogenation. J. Chem. Soc.

Japan Pure Chem. Sect. 75, 40 (1954). [Chem. Abstr.49, 10314h.]

Thiamine 89. Kawasaki, C.. and Dair4t, I. DqcQmposition of ThiamineDerivatives by Ultraviolet Irradiation. Bitamin (Kyoto)Z6. 462 (1962). [Chem. Abstr. 61, 16 350g.1

Acridine 90. Kellmann, A. Kinetics of the Photochemical Reaction ofAcridine in Alcohol. J. Chin. Phys. 56. 574 (1959).[Chem. Abstr. 53, 21088c.]

Acridine 91. Kellmann, A. Mechanism of the Photochemical Reac-tions of Acridine in Hydrogen Solvents. J. Chim. Phys.57, 1 (1960). [Chem. Abstr. 54, 12 743g.]

16

I I I I I _ _ I I I I

Acridine 92. Kellmann, A. Photodimerizatmon of Acridine and of9-Methylacri- 9-Methylacridine. J. Chim. Phys. 54. 468 (1957).

dine [Chem. Abstr. 51, 16112fi.]

Malachite 93. Kemula, W., and Gra Bowska, A. Malachite Greengreen Leucocyanide Decomposition by Light. Roczniki Chern.

34, 1445 (1960). [Chem. Abstr. 55, 12010c.]

Oxadiazoline 94. Kirmse, W. Photoreactions of an Oxadiazoline. Chem.

Ber. 93, 2357 (1960). [Chem. Abstr. a, 2623c.,

Purines 95. Kland, M. J. , and Johnson, L. A. Kinetic Study of theUltraviolet Decomposition of Biochemical Derivatives ofNucleic Acid. (Purinds). J. Am. Chem. Soc. 79 6187(1957). [Chem. Abstr. 52, 4718h.j6

Methylene 96. Koizuumi, M. , and Obata, H. Formation of Stable Semi-blue quinone of Methylene Blue by Irradiation With Visible

Light. Bull. Chem. Soc. Japan 31, 823 (1958). [Chem.

Abstr. 53, 14717a.]

Riboflavine 97. Kravchina, L. N., and Koltunova, V. I. Effect of lllu-mrination on Solutions of Crystalline Riboflavine. Tr.

Vses. Nauchn. Issled. Vitamin. last. 5, 73 (1954).[Chem. Abstr. 51, 7158f.,

Quinine 98. Kyker, G. C., McEven, M. M., and Cortatzer, W. E.Quinine Decomposition by Light. Arch. Biochem. Bio-phys. 12, 191 (1947). [Chern. Abstr. 41, 3866c.]

Triazines 99. Le F~vre, R. J. W. , and Liddiroel, T. H. Effect ofLight on I-Aryl-3, 3-dimethyltriazines, J. Chem. Soc.,

2743 (1951).

Pyridine 100. Letsinger, R. L., and Ramsay, 0. B. Pyridine Reac-tion With m- and p-Nitrophenyl Disodium Phosphate inLight. J. Am. Chem. Soc. 86. 1447 (1964). (Chem.Abstr. 60, 14347b.]

Thiamine 101. Lhuissier, M., and Biette, E. Effect of Light on Pyri-Pyridoxine doxine and Thiamine in Milk in Storage. Ann. Technol.

Agr. 11, No. 1, 63 (1962). [Chem. Abstr. 57, 5071i.1

17_ _ _ _-

Triprolidine 102, Loewenthal, L. J. A. Triprolidine Hydrochloride in thePreveintion of Some 8olar Dermatoses. Brit. J. Derya.tol. 75, Z54 (19b3). [Chem. Abstr. 60. 2232e.]

{ Piperliri.e 103. Luke., R.,* and Ferles, M. Reaction of I1-Chioro-4..S-Chloro- ethyl- and I-Chloro-4-mothyl-4-ethylpiperidine Withpiperidine Sulfuric Acid in Light. Chem. Listy 49, 510-518

(1955). [Chem. Abstr. 49, 10290d.IL O-tane 104. Margerum, J. D., Pitts, J. N., Jr., Rutgers, J. G.,Z, 2'-Din'eth- and Searles, S. Photochem 1%cal and F- Radical Dec ona-yloxetane position of Oxetane and 2, Z'-Dimethyloxetane. J. Am.

Chem. Soc. L1, 1549 (19591.

Tryptophan 105. Matsuda, G. Tryptophan Decomposition by Light.Nagasaki Igakkai Zasehi 28, 438, 811, 814, 817 (1953).

Ti [Chem. Abstr. 48, 6842d7-

Vitamins 106. Maurer, H. J., and Dittmayer, R. The Action of Ion-Riboflavine izing Radiation on Vitamins (Thiamine and Riboflavine).Thiamine Strahlentherapie 102, 531 (1957). [Chem. Abstr. 51_,

12998d.j]

Pyrone 107. de Mayo, P. Irradiation of 4, 6-Dimethyl-2-pyronc.4, 6-Dimrth- Advances in Organic Chemistry. Vol 1I, p 394. Inter-yl- 2 -pyrone airnce PFlubhi- herA. Inc. . New York, New York. 1960.

3-Indoleace- i06. Mayr, H. H. 3-indoleacetio- Acid Decomposition bytic acid Light. Planta 46, 5'2 (1956). (Chem. Abstr. 50,

7922g.]

Dipyridinium 109. Mess, G. C. Effect rf Tight on Weed Control by 1, P'-bromide Ethylene-2. 2'-dipyridinium Bromide. Ann, App1. Biol.1,lP-Ethyl- 48, 601 (1960). [Chem. Abstr. 55, 14798h.,4ene-Z, 2'-di-pyridiniumrrbromide

Tryptophan I10. Melchior, G. H. Tryptophan Decomposition by Light.Planta 50, 262 (1957). [Chean. Abstr. 5Z, 5501c.]

!1

- ----- ----- - IInsecticides III Mistric, W. J., and Martin, D. F. Insecticide Toxicity

in Relation to Sunlight. J. Econ. Entomol. 49, 757(1956). (Chem. Abstr. 51, 6070e..

Pyinimidin's 112. Moore, A, M. Ultraviolet Irradiation of Pyrimidine

HCN Derivatives. Effect of HCN. Can. J. Chem. 37, 1281(1959). [Chem. Abstr. 53, 21094d.]

Pyrimidines 113, Moore, A. M. Ultraviolet Irradiation of :Pyrimidine

Uracil Derivatives. Synthesis of the Reversible Photolysie of

"Uracii. Can. j. %.oherm. .w_, t8i (1958). tChem. Abstr,52, 6949d.I

Pyrimidine 114. Moore, A. M., and Thomson, C. H. PyrimidineDecomposition by Light. Can. J. Chem. 35, 163 (1957).[Chem. Abstr. 5i, 9331d.]

Pyrimidine. 115. Moore, A. M., and Thomson, C. H. PyrimidineDerivatives, Reaction in Light, Science 122, 594

(1955). [Chem. Abstr. 50, 4646f.]

Pyridoxal 116. Morrison, A. J.. and Long, R. F. Photolysis of P-ri-

"phosphate doxal Phosphate. J. Chem. Soc., 211 (1958j. [Chem.S~~Abotr. 5_.2, 11I035h.]

Chlorproma- 117. Nakagawa, T,, Kubota, r., and Miyazaki, H. Chlor-

zinc promazine and Promethazine Irradiation by Light. Ann. ' -.

Promethazine Rept. Shionogi Rim. Lab, 7, 19 (1957). [Chem. Abstr.51, 15279i.

Chlorproma- 118. Napolitatio, L., and Maffei, R. Allergy From Chlor-

zinc promazine. Policlinico (Rome) Sez. Prat. 64, 257y1957). [Chem. Absto. 51, dZ32-.4

a -Pyridyl- 119. Neumeyanov, A. N.., Sazonova, V. A., Gerasirnenko.

ferrocene A. V. . and Sazonova, N. S. Decomposition of Salts ofSn(-Pyridylferrocene. Dokl. Akad. Nauk SSSR 149, 1354

(1963). 'Chem. Abstr. 59, 34440h.

Tetrazoliurm 120. Nickerson, W. J., and Meckel, J. R. Effect of Light in

Ssalts Tetrazolium-Salt Reduction. Proc. Natl. Acad. Sei.U. S. 39, 901 (1953). [Chem. Abstr, 48, 8293f.

-19 I

-27

F Ribof0Lvin. 121. Nickerson, W. J. , and Strauss. G. Illmnination of AirMethionine Free Riboflavine Solution in the Presence of Methionine,

J. Am. Chem. Soc. 82, 5007 (1960).

Methylen. 122. Obats, H., Kogasaka, K., and Koirsurni, M. Photocheinl-blue cal Reaction* Between Methylene Blue and Varioue Amires

it the Presence of Oxygen. Bull. Chem. Soc. Japan 32,125 (1959). [Cbrr. Abvtr 5, 16130b.]

Methylene 123. Obata, H-, and Koizurni, M. Photochemical ReDctlona' oiue Between Methylene Blue and Tri-, Di-, and Mornomothyl

Amine. 1. Bull. Chem. Soc. Japan 3Z, 125 (1959).(Chem. Abstr. 54, 16130b.~

8 4linucli- 124. Ohnesarge, W. E., and Rogers. L. B. Fluoascence ofdinol Some Metal Chelate Compounds of 8-Quiriuclidinol.MeOWl che- Effect of Ultraviolet Irradiatirm. Spectrochirn. Act& 41lates (1958). [Chem. Abstr. 53, 13775h.]

Picrylpyri- 125. Okon, K., and Waclawek, W, Picrylpyridiniurn Chloride,dlniurn chlo- Decomposition by Light. Biul. Wojakowej Akad. Techn.ride ;0, No. 111-112, 105 (1961). FChem. Abotr. 56,

15070b.]

Pyridine 126. Oyama, T., and Miyachi, S. Pyridine Nucleotide Forma-nucleotide tion In Light, Biochim. Biophya. Acta 34, 202 (1959).

Pyrethrin 127. Page. A. B., and Blackith. R. E. Pyrethrin Decomposi-tion by Light. Pyrethrumn Post 2.No. 1, 18 (1950).

[Chem. Abstr. 44, 0587g.)

ALepin-2- 128. Paquette, L. A. The Photoieomeriaztion of 1, 3-Dihvdr'n-one deriva- 3, 5, 7-trimethyl-ZH-azepin-.2-one. j. Am. Chem. ioc.tives 86, 500 (1964).

2-Pyridores IZ9. Paq',itte, L. A., and Slomp, G. PhotdirneriZadion ofSubstituted 2-Pvridones- J. Amrn. Chem. ,.-c. 85, 765(1963).

Dipyricdyl- 130. Pirkarrpua, q, H. . and Scnger, P, Decurnposition ofethylence trans-I, Z-Dipyridylrthyienea. "rr. Dutrkjnges. Physik.

Chermi. 67, 876 ,l9,,i3. [Chem. A0.tr. 60, 6382h.

20

-NR q ý - - - -- --- I

- - 1-

ii

R iboflavine 131. Povolotakaya, K, L. , and Zaitsev.a, N. 1. Destruction ofRiboflavine Under the Influence of Visible Light. Tr.Voes. Nauchn. Iusltd. Vitamin. Init. 5, 145 (1954).[Chem. Abatr. 51, 753.

Pyrimidines 132. Prusoff, W. 11. Pyrinuldine Derivatives Irradiated by

LightýCell Sensitiz&t'on. Biochim. Biophys. Acts 58,588 (1962). [Chem. Abstr. 57, 7584b.]

Inaigo dyes 133. Pummerer, R. and Marondael. G, Optical Evidence ofthe Reversible Formation of cis- Indiqg Dyes by Means

of Irradiation. Ann. 602 228 (19571'). [Chem. Abstr. 51,10236f. ] I

3-Indoleace- 134. Ray, P. , and Curry, 0. M. Photodestruction of Indolv-tic acid 3-acetic Acid. Nature 181, 895 (19"81. (Cherr. Abstr,

52, 15266.1

Pyrimidines 135. Rice, J. M. Photochemical Addition of Benzo[a]pyreneBenzo[a]py- to Pyrimidine Derivatives (Uracil, Thymine Cytosine,:ene 5 -Methylcytonine, Guanine, and 6-Azathytnine). J. Am.Uracil Chem. Soc. 86, 1444 (1964)."rhyninas ZCytosatlIsGuanine

Pyrimidine 136. RLorech, A.. Beukere, RF. Ijistra, J. and aerandn, W.Uracil The Effect of Ultraviolet Light on Some Garponento ofThyranio the Nucleic Acids. I. Lracil, Thyrmine, 44-c. Tray.

Chirn. 77, 423 (1958). [Chem. Ab]tr, 52, 156101.1

Pyrimidine- 137. Rutter, H. A. , Jr.. 1ruetafson, L. 0. , ar Bait, W. U21.carboxylic Pyrimidinecarboxylic Acids Irradiated by Light.acids J. F'r~r~kin lust. 260, 329 (1955). [Chem, Abatr. 50,

3 904e. ]

Phe nothia- 138. Santamaria, L., Print, G., and Neri, M. Photor;.iti-Lille Isensiti- zing Action of Some Phenothiazine Derivativea. Bulil.Szers Chim. Farm. 98, 67 (1959). [Chem. Abear 53, 16386i.]

Pyriimidine 139. 3aevk0, T. , and Kin-,shita, T- Effect of Light on Toxo-Toxopyr'mi- pyrirnmdine. Ditarrmn (Kyoto) 4, 420 (1951). [Chem.dine Abstr. 46, 10-1"db,

A I

I

Mota1 corn- 140. 34hka:r, H. L. Effect -ft Light on Trmasition Mtt&l Com-plexes plae se . Acta Chl•n., AcAd. 36i. 11%•&a . 1,,,, 375 (11159).

(Chem. Abstr, .51, 11355b-1

Photochezn- 141. Schlnberg, A. Prdp~raiive O,'nienche Photochomie.

istry Springtr= Vor g. Ber!,,-Wilnerador- (Weit). Gerrvlay.

Heteracyclics 1958.(addltiona&references)

TPN (triphoo- 142. Seraydarian, M. W. TrIphosphopyridint Nucleotide

phopyeidine Response to Light. Ain 3. Physiol. 181, 291 (1955).

nuclaotide) rChem. Abhtr ,

OP N(diphos- 143. $Sraydarian. M. W., Cohen. A. I. , and Sable, H. Z

phopyridine Diphouphopyridine Nucleotide inmivation by Light. Am.

nucleotide) J. Physiol. 177, 150 (1954). fChemn. hA, 48, B293..]

Trypsin 144. Setlow, R. 1. , and Doylo, B. Trypsin I.nactivation by

Light. Arch, Biochem. Biophytt. 48, 441 (1954). (Chern.Abstr. 48, 5906(.]

1. 3-Dimneth- 145. Shih-Yi Wang. First Step in the Ultraviolet Irradiation

vyuracil oi 1, 3-Dimethyluracil. J. Ant. Chem. Soc. 80f, 6196

(1958). [Chem. Abstr. 1;3., ZIGAc.)

Pyiv'nilina•i 146. Shih-Yi Wang. Photochemicail Reacý ions in Frosen Soli-

tions of Pyriinidirne. Nature 190, 1'WU tivl)i. IGlhem,

Abstr. 55, Z3013f.]

1, 3-Dimeth- 147. Shih-Yi Wang. The Ultraviolet Irradiation 4 the Fir-t

y~luracil Product From 1, 3-Dinethyltiraci. J. Am. Chem. Sc.

80, 6199 (1958). [Chum0 Absir. 53, 221088c.

1, 3-Dimeth- 148. Shih-Yi Wang. Ultraviolet Irradiation o~f 1, 3-0-irrmethvltby-

ylthymine mine. Nature 184, 59 (19M9), [Chern. Abetv. 54, ?8'7,

1, 3-Dirneth- 149. Shih-Yi Wang, Apicelia, M. , and Stone!, B_ R. 1, 3-

ylutacii Ul0-.thy•hiracxi Decornposittoni by Light. J. A.. Cem..

Soc. 78, 4180 (1956b). Chein. Abatr. 5oI, 1524Zd.]

"TIv r Iiim'di ne I W.S .ad# tu~~ik, D.cirimrOligonu,.Aeu. !Pyrirnidin Reaidkies in 0Ieoa4a nd 54rnae aridtides i),,..le Stranded Poly; 6utI:zotidea. Proc. Intern. Congr.Polynuclir.o- Photabiol. , 3r". Cope t'-•hAge,• 1960. 6i09 (Pub. 196i1).

tides jChrrm, Abhtr. 58, 143i',0

Pyrrinidines i51. Shugir. D. . and Wierfchowuki. K. Revervible Phatolysim

Nucleic acidr• of Pyrnmiditne i) vtiive-2 lrchiudio-, Trig!s With N mcle•cA,-i,-at. Biochirti. Diuophym, AL:t&-ZJ, b57 i95 'Chemn.

Abstr. 51, 933.10..

Pyrethrin 112. Siddiqui, Ri H. , and Ma9qroud A!4, S. Stibility of Pyre-

thrin in Light. P&kibtan J. S•.c Reo. 4, 20 {1952).

[Chern. Abstr. 47, 8V61c. J

o-L•uinon 1S3. Son. 0. Light c•action of o-OQuinone Diaaides, Photo-fiiazida a-ynthesie of Cyclopentadiene and Pyrrohl Derivativ•e.Pyrrole Z. Wigs. Pth t. Photophysik Photuchrm. 30, 476 (1cyS5).

lCbhrri Absti-. 50, 835 5d, I

N-Meyti+y .2- 154. alomp, G. , MarKellar, F. A., and Paquette, L. A.pyridone Photodimer of N-Methyl-Z-pyridune. J. Arn. Cherui. SOc.

83, 4473 {19tl).

Tryptophan 155. Spies, J. R.. and Chanbers. D. G. Photochemnistry of

Conderneatain Producta. J. Am. Cheni. Soc. 70. 1682

(1048). [Chern. Abatr. 42, 6706b.]

Furaldehyde 156. Sprope, B. Decomposition of *,-Nitro- Z-furaldehydosernicarba- aermicarbarone by Light. Farm. Revy 52__, 501, 517zone (1953). [Chem. Abntr. 47, 12OCZc. 1

Riboflavine I,7, Strause, G. , ancd Nickerson, W. 1, Photochrn.ic. .i Cl-av-

age- ot Water by Riboflavine. Role of Activatrs., ). Am.

Chem. Soc. 83. 3187 (1961).

D--N (diphot-. 158. Strehier, 13. L. Luminescence in Ce'I-1rev Extract.a

plhopyridine of LurnnitIoua Bacteria and Ira AIto atfn by DFN" (DTphus-

nucleutide) phopyridirk- Nucleotide) J. Am. Chern-. Soc. 75ý. 1464(19531. [Cheir Abhtr. 47 5 4 8 0 g.z

IT

Molybdenum 159, Strohmeier, W., and Gerlach, K. The Photochemcal

carbonylpyri- Preparation of Molybdenum Pentacarbonylpyridine anddine corn- Molybdenum Tetracarbonyldipyridine. Chem. Ber. 93,pcunds 2087 (1960). (Chem. Abstr. 55, 3586d.J

Rhodopain 160. Takagi, M., and Sekoguti, Y. Effect of Iluimination onthle Ultraviolet Absorption Spectrum of R i'opsin. Bio-chim. Bicphys. Acta 49, 589 (1961). [Chem. Abstr. 55,26068c.]

Pyrethrin 161. Takei, S., Wakazono, K., and Hiraoka, K. The Changein Pyrethrin Caused by Light and Eeat. J. Agr. Chem.Soc. Japan 17, 419 (1941). [Chem. Abstr. 45, 3982g.]

Alkyl and 162, Tarkington, T. W., and Whitt, C. D. Belgian Patentaryl pyridines 614, 030 (to CLemstrand Corporation). Alkyl and Aryl2-Methyl-5- Pyridine Light Stabilizers Toward Acrylonitrile Polymer

ethylpyridine Discolo=ation. August 16, 1962. [Chem. Abstr. 5E,1581g.]

Pyrazoles 163. Tasnura, H. Pyrzolt Fungicides and Light. Bull..Nati. Inst. Agr. Sci., Apr. C., No. 5, 1-14 (1955).[Chem. Abstr. 51, 5344c.]

2-Arninopyri- 164. Taylor, E. C., and Kan. R. 0. Photochemical D-ieri-din e zation of Z-Arninop- ridines and 2-Pyridones. J. Am.2-Pyridones Chem. Soc. 85, 776 (1963).

2-Aminopyri- 165. Taflor, E. C., Kan, R. 0.: and Paudler, W. W. Pho-dines tolysis of 2-Amninopyridines and Z-Pyridories. J. Am.2-Pyridones Chemn. Soc. 83, 4484 (1961). [Chem. Abstr. 57_ 776e.

2-Pyridones 166. Taylor, E. C., and Paudler, W. W. Photodimerizationof Pvrrdones. Tetrahedron Letters,No. 25, 1 (1960).

Histi-dine 167. Tomohiro, Y. Histidine Decomposition by Light. Naga-saki igakkz-i Zasshi 28, i1i7 (1953). [Chern Abstr. 48,6

0'4 2g. I

Phenazine 168. Toromanoff, E. Molecular Association in the PhenazineScries in Relation to Photochemical Reactions.Ann. Chirn. (Paris) ., 115 (1956), [Ghern. Abstr. 52,

915ih.]

Flavinte 169. Vehara, K.,, Muraxnaku, 1. , and Makita, M. Light Acti-vation of Flavine Compounds. Bitarnin (Kyoto) 13, 261i1957). [Chemn. Misty, 54, 3542i.j

Pyrimiclne 170. Wacker, A. Dimnerization of Pyriinidine- by Light.J. Chim. Phys. 58, 1041 (1961). [Chemn. Alstr. 56,

Pyrimidines 171. Wacker, A. , Deilweg, 1-1., and Lodeinann, E. Effect of

Pvrxmidine Light on Pyrimidines and Pyrimidine Riboaldes. Angew. Iri bosides Chemn. 73, 64 (1961). [Chemn. Abstr. 55, 15573a.

"1<

Pyrimidines 172. Wackeh , A., Turager, L., and Weinblut, D. Effect ofRirosides Light on Ribosides and PyrirBidines. Angew. Chem, 73,

65 (1961). [Chem. Abstr. 55, 15573a.

Rhudopsiti 173. Wald, G. Rhodopsin System and Light. The Photochemi-cal Basis of Rod Vision. J. Opt. Soc. Am. 41, 949(1951). [Chem. Abstr 46. 3139g.]

Rhodopsin 174. Wald, G., and Brown, P. K. Sulfhydryl Group-Role in

3577(c2.flarA~t A7A1Bleaching and Synthesis of Rhodopain. J. Gen. Physiol.

Tetrarolium 17.5. Weygand, F., and Fre'nk, 1. Tetrazolium Compounds-Compounds Decomposition in Light. (2, 3, 5-Triphenyltetrazoliurn

Ghlo r iC de). Z. Naturforsch. 3b, 377 (1948). [Chem.Abstr. 43, 5313f.1

Pyrimidine 176. Wierzchowski, K., and Shugar, D. Decomposition4oeAiino- of 4-Arninopyriiidines. Proc. Intern. Congr. Photo-

pyrimidines biol. , 3rd, Copenhagen 1960, 606 (Pub. 19614. [Chem.Abstr. 58, 9783h. ]

Polymers 177. Williamd, J. Los. R.y and Borden, L. G. PhotoreactivePyridirdnlin Polymer-1i, 2- (Aryivinyl)-N -vinyipyridinium Arene Sul-salts fonate Polymers. Makron.ol. Chem. 73, 203 (1964).

[Chein. Abstr. 61, 7371h.

Ainnopterin 178. Williams, 5. N.a , Jr. Decomposition by Light of ARninop-teri and Folic arid. J. Biol. Chrm. 187, 47 (1950).[Chern. Abstr. 4S, 3879d.

25

• -- • • • -- =- • • _• • . .. ---.... - i- ,

Thiamine 179. Wotherspoon, N., and Oater, G. Light Induced Spectraldye s Shift of the Thiazine Dyes in the Bound State (Polyacrylic

Acid). J. Am. Chem. Soc. 79, 3992 (1957). [Cheri.,Abetr. 52, 98c.]

Rhodopsin 180. Wulff, V. J., Adams, R. G. , Linschitz, H., and Abra-haineon, E. W. Effect of Flash Illumination on Rhodopsinin Solution. Ann. N. Y. Acad. SO. 74, Art. 2,281(1958). [Chem. Abstr. 53, 631 lb. ]

Methylene 181. Yoshida, Z., and Kazamna, K. Methylene Biuo Decompo-blue •ition by Light. Kogyo Kagaku Zasshi 59, 1418 (1956).

[Chem. Abstr. 53, 2821i.]

Methylene 182. Yoshida, Z., and Kazama, K. Photosensitized Reductionblue of Benzophenone by Methylene Blue. Kogyo Kagaku

Zasshi 60, 195 (1956). [Chem. Abstr. 53, 2822b.]

Rhodopsin 183. Yoshizawa, T., and Kito, Y. Rhodopsin Illuminated atLow Temperatures. Ann. Rept. Sci. Works Fac. Sci.Osaka Univ. 6, 27 (1958). [Chem. Abstr. 53, 7783g.]

Pyridine 184. You Sun Kin and Yong Ja Park. Reaction of PyridineWith Organic Halides in Ultraviolet Light. Ta Han HuaHsueh Hui-Chih 6, 148 (1962). [Cheor. Abstr. 60,2476b. ]

Methylene 185. Yushina, V. V., and Nikolaev, L. A. Methylene Blueblu: Reaction With Amines in Light. Zh. Fiz. Khim. 37,

2277 (1963). [Chern. Abstr. 60. 4279a.]

Acridine 186. Zanker, V. , Cnobloch, H., and Mader, F. UltravioletSpectroacopical and Photochemical Behavior of Acridine.Proc. Intern, Syrup. Mol. Struct. Spectry. (Tokyo)B 302/14 (1962). [Chem. Abstr. 61, 207g. j

Acridine 187. Zanker, V., and Peter, W. Acridine and Fluoresceindyes Dyes. Z. Physik. Chem. (F'rankfurt)26, 159 (1960).Fluorescein [Cheor. Abstr. 55, 7007b. ,dyes

Dypnone 188. Zimmerman, H. E. Photolysis of trans-Dypnone Oxideoxide Advances in Photochemistry. Vol 1, p 199. Interscience

Pullishers, Inc., New York, New York. 1963.

26

' i-iiiiIIIII IIIIIIIII

III. KEYWORD INDEX.

Acridan 56

SAcridine 56, 79, 80, 91 92, 186Acridine dyes

187Adenosine triphosphate

31Alkylpyridine 162

Aminopterin 178j2-Arninopyridines

164, 1654 -Amninopyrimidines 176Arylpyridine 162

ATP?31 -Aza-3, 5, .-trimethylcyclohepta-4, 6-dien-2-one 32Azepin-2..one derivatives

128

4-Azidapyridine 77

1, 2tBenzisothiazolin-3 -one- 1, i-dioxide 78Benzo[a]pyrene 135

2, 2'-Benzothiazyl disulfide 35.Benzotriazole derivatives

823Benzotriazoles 10S4, 4 '-Bipyridine 85

2, Z'-Bipyridine 73Garbazole 20

'i- *arbostyr~1 27S~27

1 -Chloropiperidine 103

Chlorpromazine 117, 118Cytosines

135Diazirine

3. 492, 2 '-Dimethyloxetane

1044, 6 -Dimethyl- 2-pyrone 1072, 4 -Dirnethylthiazole

8Dihydropyridine

139 - Dihydroxyquinoxaline 88

1, 3 -Dimethylthymine 1481. 3-Dimethyluracil

145. 147Dinitrobe nzylpyridine

41Dinucleotides

84Diphenylamine 20Diphosphopyridine nucleotide 31, 143, 158

Dipyridinium bromide 109

Dipyridyl 30Dipy ridylethylenes

130DPN

31, 143, 158

27

+• - -++ - - -+ - +--. -• . .. _• +

Dypnone oxideide 181, i I-Ethylene-2, 21-dipyridtnittm bromide 109

Ethylene oxide 58Ferric @&Its 73

Ferrocyanide-2, 2'-bipyridine; ferrocyanide- 1, 10-phenanthroline 6Flavines 1 19Formanane 65, 66Furaldehyde sen¢icarbazono 156Guanine: 135HCN 112Histamine 47, 53

$ Hiatidine 2, 47, 53, 167Hydroxypyrimidines 835-Hydroxytryptophan 42Imidazole 53Indigo dyes 133Indole 593-Indoleacetic acid 14, 15, 21-23, 108, 134Insecticides 111Iridium pyridine derivatives 36, 37Ketones 12Malachite green 9

Malononitrile derivatives 11SMetal chelates 11A •

SMetal complexes 140Methionine 1219-Methylacridine 79, 92N-Methylcarbostyril 27Methylene blue 4, 41, 96, 122, 123, 181, 182, 1852-Methyl-5-ethylpyridine 162N-Methyl- 2-pyridone 34, 154Methyl pyridyl glycol 12Molybdenum carbonylpyridine compounds 159Nicotinamide 2Nitrobenzylpyridinee 61Nucleic acids 149Oligonucleotides 150Oxadiazoline 94Oxetane 104Phe nazine 168Phenothiazine 75Phenothiazine sensitizers 138Phenyl pyridyl glycol 12

28

- -

r[ Phe nyl( 2 -thie nylmethyle ne )malononit rile I1I

L Photography 92 -Picoline -N -oxide 6n

S3 -Picoline -N -oxide 63

T: Picoline sensitizer 9

SPicrylpyridinium chloride 125PiperidinePolymers 177Poly nucleotides 150

Promethazine 117Pseudomonads pigment 43Purines 95

SPyove rdine 43

W Pyrazoles 163Pyrethrin 17, 127, 152, 161

÷Pyrethrumn 57

Pyridine 29, 45, 46, 50, 100, 184Pyridine-N-oxide 64Pyridine nucleotide 126Pyridines 50, 51

I l:Pyridine sensitizer 9Pyridinium salts 177Pyridonee 52-Pyridones 129, 164-166Pyridoxal phosphate 116

- Pyridoxine 101Pyridylacrylic acid 67a -Pyridylferrocene 119Pyridyl glycols 12Pyridyl ketones 12Pyrimidine 114, 136, 139, 172, 176Pyrimidinecarboxylic acids 137Pyrimidine ribosides 171Pyrirr.idines 16, 87, 112-115, 132, 146, 149, 150, 171, 172

ik Pyrone 1072-Pyrone 34Pyrroles 153Quinine 98 AQuinine hydrochloride 38Quinoline -N -oxide 26Quinoline - N -oxides 28o-Quinone diazides 153Quinoxali ne s 88

29 ._ __ ___

• • . m l I I I I

g II

8 -Quinuclidinol 124

"Rhodium pyridine derivatives 36, 37

Rhodopsin 1, 18, 24, 25, 60, 160, 173, 174, 180, 183

Riboflavine 54, 68-72, 76, 97, 106, 121, 131, 157

XRbosides 171, 172

Se rotonin 42

Silver dipyridyls 30

Spiraea 41

Sullonamide 75

Tetrazolium compounds 66, 81, 175

Tetrazolium salts 120

Thiamine 89, 101, 106

Thiamine dyes 179

Thiophe nes 55

Thiopyronine 19

Ihiourea 4

Thyrnine 136

Thymine dimers 84

Thyrnineo 135

Toxopyrirnidine 139

TPN 142

Triazines 48, 86, 99

Triphenylformazan 66

Triphenyltetrazolium chloride 66Triphosphopyridine nucleotide 142

j Triprolidine 102Trp~r~ • -144

Tryptophan 14, 15, 39, 40, 105, 110, 155

Uracil 33, 113, 135, 136

Viologens 85

Visual pigments 24, 25

Vitamin B2 70

Vitamins 106

Xanthylidineanthrone 41

Yeast 8

S0

-1

30 |i I I I I I I I I I I II I

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32

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4 ~ ~ ~ ~ ~ ~ * 'Tt 'TVfý otOR11DY 69UNJIY C L.4*81PSCAION

-- 3Ara,, 2 UNCLASSIFIED

rN A

OFI-r-ERT-1-CICCOMIPOUNDS

.. • duri ep'ember 1965.

I j 7,. T YAt- 4~O AK b NO. OFOP9 ftupU

ýs 6• 37

EASP 100-4

!-yo. 1C622401A10204 9b. oTan P o c(S) (Any eieremob/O tmabe.Df.d

-1LITY/LiilrA" .•oT•,cts This document is subject to specia! export controlsa ~ eaI.h transmittal to foreign governments or foreign nationals may be made,-ý,wy w:i.h prior approval of the Commanding Officer, US Army Edgewood Arsenal,ATTN: ;SMUEA-TSTITo EdgewoodArsenal, Maryland 21010.

1 -,U•Pt4: vIT.AV NOT%$ I. SPONSORING MILITARY ACTIVITY

D :-:,n and warning investigations N/A

A• • T• (U) The literature on the photochemistry of heterocyclic compounds

Sv•i" 6 i Vey•d with a particular interest in pyridine chemistry. This listing of-• • :e8-;as compiled as a result of searching volumes 41 to 61 of ChemicalA -.1- tA under the headings light, photochemistry, and pyridine.

1-- <YWORDS.•crature survey Irradiation

-Irocyclid compounds Stability.tochernistry Decomposition• dine s Ultraviolet light:te oion Photosensitivity

i 1. -theais •Photochromism,ztion mechanisms Illuminationo -tographv Luminescence

FluoreecenceS• otolyeis SSensitizers

; : ,4-? 37 UNQASSifeDSpeud~ty Cl4*Aesufte~u