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Volume II
COMPOUNDS OF GERMANIUM, TIN AND LEAD
INCLUDING BIOLOGICAL ACTIVITY AND COMMERCIAL APPLICATION
ORGANOMETALLIC COMPOUNDS
METHODS OF SYNTHESIS
PHYSICAL CONSTANTS AND CHEMICAL REACTIONS
Edited by
MICHAEL DUB
Central Research Department, Monsanto Company
Volume II
COMPOUNDS OF GERMANIUM, TIN AND LEAD
INCLUDING BIOLOGICAL ACTIVITY AND COMMERCIAL APPUCA TION
Second Edition, Edited by
RICHARD W. WEISS
Organic Division, Monsanto Company
Covering the Literature from 1937 to 1964
Springer Science + Business Media, LLC 1967
ORGANOMETALLIC COMPOUNDS Second Edition
VoI. 1 - Compounds of Transition Metals, published in 1966
VoI. IlI-Compounds of Arsenic, Antimony, and Bismurh, in preparation
ISBN 978-3-642-51891-1 ISBN 978-3-642-51889-8 (eBook) DOI 10.1007/978-3-642-51889-8
AII rights reserved, especially thar of teanslatiao into foreigo languages
It is also forbidden tO reproduce this book, e'ther whole or in part, by phoromechanical meanS
(photostat, microfilm andlor microcard Ot any other means)
wirhout written permission from the Publisbers
© 1967 by Springer Scienee+Business Media New York Originally published by Springer-Verlag New York, Ine. in 1967
Library of Congress Catalog Card Number 66-28249
Tirle No. 4358
PREFACE TO THE SECOND EDITION
The aim of this compilation has been to provide a comprehensive, noncritical source of information concerning organometallic compounds. The scope is limi~ed to the compounds containing at least one carbon-metal bond. The information includes methods of preparation, properties, chemical reactions, and applications.
The First Edition comprised the literature from 1937 to 1958. The Second Edition is completely revised and extended through 1964. The literature prior to 1937 was thoroughly covered by E. Krause and A. von Grosse in ''Die Chemie der metall-organischen Verbindungen," Verlag von Gebrueder Borntraeger, Berlin, 1937.
Our work consists of three volumes. Volume I contains derivatives of the transition metals of Groups III through VIII of the Periodic Table. Volume II contains derivatives of germanium, tin, and lead. Volume III contains derivatives of arsenic, antimony, and bismuth.
The compilation is based on searches through Chemical Abstracts. The collection of references for 1964 was completed before the Subject Indexes to Volumes 60 and 61 of the Abstracts were available; thus some omissions in the coverage of that year are possible.
We have attempted to make the .. coverage of the literature complete in order that the compilation may have best ~i1ity to the chemist, chemical engineer, patent attorney, and editor. In the interest of brevity, certain numerical data are omitted, but references to the original literature are given. Yield data are rounded to two significant figures. Wherever possible, tables have been used. The entries in the Bibliography section include references to Chemical Abstracts.
I am indebted to Dr. R. S. Gordon, Director of the Central Research Department, and to Mr. W. A. Wilkinson, Head of the Information Center, Monsanto Company, for their generous support of this project. I am also indebted to Dr. R. W. Weiss, the Coeditor of Volume 11, for his invaluable advice on the form of this compilation. My thanks are due to the library staff at the Information Center for their assistance and especially to Mrs. Mary Alice Doiron for the preparation of the typescript for the photo-offset printing.
St. Louis, Missouri January 1966
V
Michael Dub
INTRODUCTION TO VOLUME II
Volume II of the series ''Organometallic Compounds" covers organic derivatives of germanium, tin, and lead. The term organometallic compound is used in the strictest sense and includes only compounds with at least one metalcarbon bond. We attempt to present complete information on the organic derivatives of the three metals. Literature.data for each compound are given in separate paragraphs on SyntheSis, Properties, Chemical Reactions, and Addition Compounds. Two new entries not covered in Volume I for Use and Biological Properties are added. This recognizes the commercial interest reflected in numerous publications connected with the industrial application of organometallic derivatives of tin and lead.
To facilitate the use of this volume and to allow correlation of analogous organometallic derivatives of germanium, tin, and lead, the individual compounds are listed systematically. A decimal system is used to characterize chapters and subchapters. Similar compounds of each metal can be found under corresponding numbers. The system and arrangement will be obvious from the Table of Contents. The main chapters are as follows:
1. Symmetric tetraorganometal compounds - R4M 2. Unsymmetric tetraorganometal compounds - RnMR'4-n 3. Organometal hydrides - Rn~-n 4. Organometal compounds containing heteroatom-metal bonds - RnMX4-n 5. Organo-polymetal compounds, e.g. ReSQ2 6. Bimetallic compounds, e.g. R3PbLi 7. Cyclic organometal compounds, e.g. CH2(CH2)3Ge~ 8. Polymerization reactions and unspecified compounds 9. Commercial application.
The arrangement within the main chapters follows three simple principles: order with decreaSing number of metal-carbon bonds; order with increaSing complexity of organic groups; consistent use of a sequence of heteroatoms.
The compounds are listed in order of the organic moieties linked to the central metal in the series aliphatic, aromatic, heterocyclic, unsaturated, and functionally substituted groups; aralkyl groups are arranged according to the location of the carbon-metal bond within the above series. The following examples illustrate location of certain groups: benzyl follows methyl but precedes ethyl; tolyl follows phenyl and precedes naphthyl; and 2-indenyl or 9-fluorenyl follows cyclopentadienyl.
The sequence of the heteroatoms as substituents follows the reverse of their position in the Periodic Table, i.e., halogen, oxygen and homologues, nitrogen and homologues, etc. A group of closely related substituents, with often uncertain linking atoms, is listed as pseudohalides and follows halogen. This group comprises (iso)cyanide, (iso)cyanate, (iso)thiocyanate, azide, and cyano complexes. All salts or esters of oxygen acids, excluding
VII
carboxylic acids, are combined under Salts. Polyfunctional groups are listed under the heteroatom next to the central metal or under the function first appearing in the system. Cross references are given. The nomenclature is generally in agreement with Chemical Abstracts.
For helpful discussions and criticisms my thanks are due to my colleagues Drs. M. W. Dietrich, B. Dmuchovsky, and Q. E. Thompson. I am indebted to Mary Alice Doiron for the preparation of the typescript and her skill in arranging the tables. I am glad to acknowledge the contributions of Erika Weiss in collecting and checking references, technical assistance, and reading the proof.
Monsanto Company Organic Division St. Louis, November 1966
R. Weiss
VIII
ABBREVIATIONS
The following abbreviations are used in addition to, or at variance with, those in Chemical Abstracts:
cat. corr. dec. DMF
Fc GLC IR liq. m. M
mat!. obtd. prod. psi PVC Py ref. r. t.
rxn. sub!. substd. THF TLC
UV
catalyst corresponding decomposition, d~composes, decomposed, decomposing dimethylformamide ferrocenyl radical, CsHsFeCs14-gas-liquid chromatography infrared liquid (adjective) melting point, melts at, melted at a metal atom in generic formulae material(s) obtained product{s) pound per square inch pressure polyvinyl chloride pyridine re ference( s) room temperature reaction( s) sublimes at, sublimed at, sublimation substituted tetrahydrofuran thin-layer chromatography ultraviolet
IX
CONTENTS
PREFACE TO THE SECOND EDITION III
INTRODUCTION TO VOLUME II V
ABBREVIATIONS VII
GERMANIUM
2. 2.1 2.4 2.4.1
2.5
2.5.1
2.6 2.6.1 2.6.2 2.6.3 2.6.3.1 2.6.3.3 2.6.3.4 2.6.4 2.6.5 2.7 2.7.1 2.7.2 2.7.3 2.7.6 2.7.7
3. 3.1
3.2 3.3 3.6 3.8
SymmetriC Tetraorganogermanes 1
Unsymmetric Tetraorganogermanes Nonfunctional Derivatives 4 Unsymmetric Tetraorganogermanes with Olefinic Substituents 13 Unsymmetric Tetraorganogermanes Containing Functionally
Substituted Olefinic Groups 19 Unsymmetric Tetraorganogermanes with Acetylenic Sub-
stituents 19 Unsymmetric Tetraorganogermanes Containing Functionally
Substituted Acetylenes 24 Functionally Substituted Unsymmetric Tetraorganogermanes 27 Tetraorganogermanes Containing Halogen 27 Tetraorganogermanes Containing Pseudohalogen Substituents 28 Tetraorganogermanes Co~taining Oxygen 32 Organogermanes with Hydroxy Groups and Their Derivatives 32 Tetraorganogermanes Containing Carbonyl Groups 36 Tetraorganogermanes Containing Carboxyl Functions 38 Tetraorganogermanes Containing Sulfur 42 Tetraorganogermanes Containing Nitrogen and Phosphorous 42 Tetraorganogermanes Containing Metal Substituents 45 Bridged Bisorganogermanes 45 Tetraorganogermanes Containing Organosilyl Substituents 48 Tetraorganogermanes Containing Organotin Substituents 48 Tetraorganogermanes Containing Group II Metals 51 Tetraorganogermanes Containing Alkali Metals 52
Organogermanium Hydrides Nonfunctional Organogermanium Hydrides Unsymmetric Organogermanium Hydrides Deuterium-Substituted Organogermanium Hydrides Functionally Substituted Organogermanium Hydrides Organogermanium Hydrides Containing Heteroatom-
Germanium Bonds Mixed Organogermanium Hydride Halides Organogermanium Hydrides Containing Other Germanium
Heteroatom Bonds
XI
52 58 59 59
4.
4.1 4.1.1 4.1.1.1 4.1.1.2 4.1. 1.6 4.1.2 4.1.2.1 4.1.2.6 4.1.3 4.1.3.1 4.1.3.4 4.1.3.6 4.2 4.2.1 4.2.4 4.3 4.3.1 4.3.1.1 4.3.1.2 4.3.1.3 4.3.2 4.3.3 4.3.5 4.3.5.1
4.3.5·6
4.4 4.4.1 4.4.2 4.4.7 4.5
5. 5.1 5·2
5.3
6. 6.1 6.5
Organogermanium Compounds Containing Heteroatom-Germanium Bonds
Compounds with Halogen Triorganogermanium Halides Unsubstituted Symmetric Triorganogermanium Halides Unsymmetric Unsubstituted Triorganogermanium Halides Functionally Substituted Triorganogermanium Halides Diorganogermanium Dihalides Unsubstituted Diorganogermanium Dihalides Functionally Substituted Diorganogermanium Dihalides Organogermanium Trihalides Unsubstituted Organogermanium Trihalides Unsaturated Organogermanium Trihalides Functionally Substituted Organogermanium Trihalides Organogermanium Salts Organogermanium Pseudohalides Organogermanium Salts or Esters of Oxygen Acids Organogermanes with Germanium Oxygen-Bonds Organogermanium Oxides and Hydroxides Triorganogermanium Oxides and Hydroxides Diorganogermanium Oxides Monoorganogermanium Oxides and Germanoic Acids Organogermanium Peroxy Compounds Organogermanium Alkoxides and Mixed Oxides Organogermanium Carboxylates Organogermanium Carboxylates with Unsubstituted
Carboxylic Acids Organogermanium Carboxylates Derived from Functionally
Substituted Carboxylic Acids Organogermanium Compounds with Sulfur and Selenium Organogermanium Sulfides, Disulfides, and Selenides Organogermanium Mercaptides and Mercaptans Metal-Substituted Organogermanium Sulfides and Selenides Organogermanium Compounds with Nitrogen, Phosphorous,
Arsenic, Antimony, and Bismuth Organogermanium Amides, Imides, Nitrides, and Phosphides Organogermanium Metal Imides Organogermanium Imido Phosphoranes and Arsenic or
Antimony Analogues
Organo-polygermanes Hexaorganodigermanes Organo-polygermanes Containing More Than Two Germanium
Atoms Organo-polygermanes Containing Heteroatoms
Bimetallic Organogermanes Organogermanes Containing Germanium-Metal Bonds Bimetallic Organogermanium Derivatives with Metal
Coordination Compounds
XII
65 65 65 70 70 77 77 79 83 83 85 89 93 93 93 99 99 99
102 102 104 106 112
112
112
119 119 121 123
125 125 125
125
128 129
130 132
133
138
7.4.1 7.4.3
7·5
8.1
TIN
1. 1.1 1.3 1.4 1.6
1.6.1 1.6.2
2. 2.1 2.3 2.4 2.4.1
2.6
2.6.1 2.6.2 2.6.3 2.6.3.1 2.6.3.2 2.6.3.3 2.6.3.4 2.6.4 2.6.5.1 2.6.5.2 2.7
Cyclic Organogermanes Cyclic Tetraorganogermanes Cyclic Organogermanium Hydrides Cyclic Organogermanium Compounds Containing Heteroatom-
Germanium Bonds Cyclic Organogermanium Halides Cyclic Organogermanes with Germanium-Oxygen Bonds Cyclic Organo-polygermanes
Polymerization Reactions with Organogermanes
Symmetric Tetraorganotin Compounds Nonfunctional Symmetric Tetraorganotin Compounds Symmetric Tetraheterocyclic Tin Compounds Symmetric Unsaturated Tetraorganotin Compounds Symmetric Functionally Substituted Tetraorganotin
Compounds Symmetric Halogen-Substituted Tetraorganotin Compounds Other Symmetric Functionally Substituted Tetraorgano
tin Compounds
Unsymmetric Tetraorganotin Compounds Unsymmetric Nonfunctional Tetraorganotin Compounds Heterocyclic Substituted Tetraorganotin Compounds Tetraorganotin Compounds with Olefinic Substituents Tetraorganotin Derivatives of Functionally Substituted
Ole fins Tetraorganotin Compounds with Acetylenic Substituents Functionally Substituted Tetraorganotin Derivatives of
Acetylenes Functionally Substituted Unsymmetric Tetraorganotin
142 l~
150 150 153 155
155
172 172
172
176 177 190 193
198 210
211
Compounds 217 Tetraorganotin Compounds Containing Halogen 217 Tetraorganotin Compounds Containing Pseudohalogen Groups 218 Unsymmetric Tetraorganotin Compounds Containing Oxygen 225 Compounds Derived from a Hydroxy Group 225 Peroxy Tetraorganotln Compounds 229 Organotin Compounds Containing Carbonyl Groups 229 Tetraorganotin Compounds Containing Carboxyl Groups 233 Tetraorganotin Compounds Containing Sulfur 238 Tetraorganotin Compounds Containing Nitrogen 240 Tetraorganotin Compounds Containing Phosphorous 240 Tetraorganotin Compounds Containing Organometallic
Substituents 244 Bridged Organotin Compounds 244 Tetraorganotin Compounds with Organosilyl Substituents 2~
Tetraorganotin Compounds with Organogermanium Substituents 2~
XIII
2.7.4 2.7.5 2.7.6 2.7.7 2.8
3. 3.1
3.3 3.5 3.6
4. 4.1 4.1.1 4.1.1.1 4.1.1.2
4.1.1.3 4.1.1.4 4.1.1.6 4.1.1.6.1 4.1.1.6.2
4.1.1.6.3 4.1.1.6.5 4.1.1.6.7 4.1.2 4.1.2.1 4.1.2.3 4.1.2.4 4.1.2.6 4.1.2.6.1 4.1.2.6.2
4.1.2.6.3 4.1.2.6.9 4.1.3 4.1.3.1 4.1.3.3 4.1.3.4 4.1.3.6 4.1.3.6.1 4.1.3.6.9 4.1.4 4.1.4.1
4.1.4.3 4.1.4.5
4.1.5 4.2
4.2.1 4.2.4
Tetraorganotin Compounds with Organolead Substituents Tetraorganotin Compounds with Boron and Aluminum Tetraorganotin Compounds with Group II Metals Tetraorganotin Compounds with Group I Metals Tetraorganotin Compounds with Tin-Carbon Double Bonds
Organotin Hydrides
Nonfunctional Organotin Hydrides Organotin Deuterides Functionally Substituted Organotin Hydrides Organotin Hydrides Containing Heteroatom-Tin Bonds
Organotin Compounds Containing Heteroatom-Tin Bonds
248 252 252 254 254
254
255 265 265 265
Organot in Hal ides 268 Triorganotin Halides 268 Symmetric Unsubstituted Triorganotin Halides 268 Unsymmetric Unsubstituted Triorganotin Halides 286 Heterocyclic Substituted Triorganotin Halides 290 Unsaturated Triorganotin Halides 290 Functionally Substituted Triorganotin Halides 290 Halogen-Substituted Triorganotin Halides 290 Pseudohalogen-Substituted Triorganotin Halides 290 Oxygen-Containing Triorganotin Halides 290 Nitrogen-Substituted Triorganotin Halides 290 Metal-Substituted Triorganotin Halides 290 Diorganotin Dihalides 302 Unsubstituted Diorganotin Dihalides 302
Heterocyclic Substituted-Diorganotin Diha1ides 315 Unsaturated Diorganotin Dihalides 321 Functionally Substituted Diorganotin Dihalides 322 Halogen-Substituted Diorganotin Dihalides 322 Pseudohalogen-Substituted Diorganotin Dihalides 322 Oxygen-Substituted Diorganotin Dihalides 322 Diorganotin Dihalides Containing Nitrogen or Silicon 322 Organotin Trihalides 327 Unsubstituted Organotin Trihalides 328 Heterocyclic Organotin Trihalides 333 Unsaturated Organotin Trihalides 333 Functionally Substituted Organotin Triha1ides 333 Halogen-Substituted Organotin Trihalides 333 Organotin Trihalides with Substituents Other Than Halogen 333 Organotin Halides Containing Tin-Oxygen Bonds 336 Organotin Halides Containing Oxy- or Hydroxy-Groups 337 Organotin Halides Containing Alkoxy Groups 337 Organotin Halides Containing Carboxylate Groups 342
Organotin Halides Containing Tin-Sulfur Bonds 342 Organotin Salts 344 Organotin Pseudohalides 344
Organotin Salts or Esters of Oxygen Acids 347
XIV
4.; 4.;.1 4.;.1.1 4.;.1.2 4.;.1.2.1
4.;.1.2.6
4.;.1.; 4.;.2 4.;.; 4.;.;.1 4.;.;.1.;
4.;.;.1.6.1
4.;.;.1.6.;
4.;.;.1.6.7
4.;.;.1.9 4.;.;.2 4.;.;.2.1 4.;.;.2.;
4.;.;.2.6.1
4.;.;.2.6.;
4.;.;.2.9 4.;.;.2.9.1 4.;.;.2.9.2 4.;.;.; 4.;.4 4.;.5 4.3.5.1
Organotin Oxygen Compounds Organotin Oxides and Hydroxides Triorganotin Oxides and Hydroxides Diorganotin Oxides and Hydroxides Nonfunctionally Substituted Diorganotin Oxides and
Hydroxides Functionally Substituted Diorganotin Oxides and
Hydroxides Monoorganotin Oxides and Hydroxides Organotin Peroxy Compounds Organotin Alkoxides Triorganotin Alkoxides and Phenoxides Triorganotin Alkoxides Derived from Heterocyclic
Alcohols Triorganotin Alkoxides Derived from Unsaturated
Alcohols Triorganotin Alkoxides Derived from Functionally
Substituted Alcohols Triorganotin Alkoxides Derived from Halogen-Sub
stituted Phenols Triorganotin Alkoxides Derived from Alcohols or
Phenols Containing Oxygen Functions Triorganotin Alkoxides Derived from Alcohols or
Phenols Containing Nitrogen Triorganotin Alkoxides Derived from Organometallic
Substituted Alcohols or Phenols Triorganotin Mixed Oxides Diorganotin Alkoxides Unsubstituted Diorganotin Alkoxides and Phenoxides Diorganotin Alkoxides Derived from Heterocyclic
Alcohols Diorganotin Alkoxides Derived from Functionally Sub
stituted Alcohols and Phenols Diorganotin Alkoxides Derived from Halogen-Substi
tuted Phenols Diorganotin Alkoxides Derived from Alcohols or Phenols
;71 ;75 ;78 ;81 ;81
;8;
;8;
;8;
;92 ;92 ;95 ;95
400
400
400
Containing Oxygen Functions 400 Diorganotin Alkoxides Derived from Alcohols or Phenols
Containing Nitrogen 400 Diorganotin Alkoxides Derived from Dihydric Alcohols
or Phenols Miscellaneous Diorganotin Alkoxides Diorganotin Siloxanes Diorganotin Alkoxide Carboxylates Monoorganotin Trialkoxides Organotin Derivatives of Acetals Organotin Carboxylates Triorganotin Carboxylates
xv
400 400 400 400 408 408 408 408
4.3.5.1.1 4.3.5.1.3
4.3.5.1.6.8.1 4.3.5.1.6.8.2
4.3.5.1.9.1 4.3.5.1.9.2
4.3.5.1.9.3 4.3.5.2 4.3.5.2.1 4.3.5.2.3
4.3.5.2.6 4.3.5.2.6.1 4.3.5.2.6.3
4.3.5.2.6.8 4.3.5.2.9 4.3.5.3 4.4 4.4.1 4.4.1.1 4.4.1.2 4.4.1.3 4.4.2 4.4.2.1 4.4.2.1.1
4.4.2.1.3 4.4.2.1.6
Unsubstituted Triorganotin Carboxy1ates Unsubstituted Triorganotin Carboxy1ates Derived
from Heterocyclic Acids Unsubstituted Triorganotin Carboxy1ates Derived
from Unsaturated Acids Unsubstituted Triorganotin Carboxy1ates Derived
from Functionally Substituted Acids Unsubstituted Triorganotin Carboxy1ates Derived
from Halogen-Substituted Acids Unsubstituted Triorganotin Carboxy1ates Derived
from Oxygen- and Sulfur-Containing Acids Unsubstituted Triorganotin Carboxy1ates Derived
from Acids Containing Nitrogen Unsubstituted Triorganotin Carboxy1ates Derived
from Acids Containing Mercury Unsubstituted Triorganotin Carboxy1ates Derived
from Po1yfunc~iona1 Acids Bis-Triorganotin Derivatives of Dicarboxy1ic Acids Unsubstituted Triorganotin Carboxy1ates Derived
from Po1yfunctiona1 Acids Unsymmetric or Functionally Substituted Triorgano
tin Carboxylates Unsymmetric Triorganotin Carboxy1ates Unsymmetric Triorganotin Carboxy1ates Derived
from Functionally Substituted Acids Functionally Substituted Triorganotin Carboxylates Diorganotin Carboxylates Unsubstituted Diorganotin Carboxy1ates Diorganotin Derivatives of Heterocyclic and
Unsaturated Carboxylic Acids Functionally Substituted Diorganotin Carboxy1ates Halogen-Substituted Diorganotin Carboxylates Diorganotin Carboxy1ates Derived from Acids Substi-
410
417
420
420
420
420
420
426 426
426
426 426
426 426 433 433
439 442 442
tuted with Oxygen, Sulfur, Nitrogen, and Phosphorous 442 Diorganotin Carboxylates of Dicarboxy1ic Acids 442 Diorganotin Carboxy1ates Containing Tin-Sulfur Bonds 446 Monoorganotin Carboxylates 448 Organotin Compounds with Sulfur, Selenium, and Organotin Sulfides, Se1enides, and Tellurides
Tellurium 451 451
Triorganotin Sulfides, Selenides, and Tellurides Diorganotin Sulfides, Selenides, and Tellurides Monoorganotin Sulfides and Selenides Organotin Mercaptides and Organoselenides Triorganotin Mercaptides Unsubstituted Triorganotin Mercaptides and Organo-
selenides Heterocyclic Substituted Triorganotin Mercaptides Functionally Suhstituted Triorganotin Mercaptides
XVI
451 453 456 456 456
4.4.2.2 4.4.2.2.1 4.4.2.2.3 4.4.2.2.6 4.4.2.3 4.4.4 4.4.7
4.5.1 4.5.2 4.5.3 4.5.4 4.5.5 4.5.6
5.3 5.4
6. 6.1 6.4 6.5
7. 7.1 7.3 7.5
8. 8.1 8.2
9.
LEAD
1. 1.1
1.3 1.4 1.6
Diorganotin Dimercaptides 462 Unsubstituted Diorganotin Dimercaptides 462 Heterocyclic Substituted Diorganotin Dimercaptides 464 Functionally Substituted Diorganotin Dimercaptides 465 Monoorganotin Trimercaptides 468 Organotin Thiocarboxylates, Xanthates, and Thiocarbamates 470 Metal-Substituted Organotin Sulfides, Selenides, and
Tellurides Organotin Compounds with Nitrogen, Phosphorous, Arsenic,
Antimony, and Bismuth Unsubstituted Organotin Amides, Imides, and Nitrides Heterocyclic Organotin Imides Organotin Derivatives of Acid Amides and Acid Imides Organotin Metal Imides Organotin Imido Phosphoranes and Imido Stibanes Organotin Phosphides, Arsenides, Antimonides, and
Bismuthides
Organo-Polytin Compounds Hexaorganoditin Compounds Organo-Polytin Compounds Containing More Than Two Tin
Atoms Organo-Polytin Halides Organo-Polytin Carboxylates
Bimetallic Organotin Compounds Organotin Derivatives of Groups II-IV Elements Organotin Alkali Metal Compounds Organotin Derivatives with Transition Metal Coordina
tion Compounds
Cyclic Organotin Compounds Cyclic Tetraorganotin Compounds Cyclic Organotin Compounds with Heteroatom-Tin Bonds Cyclic Organo-Polytin Compounds
Miscellaneous Organotin Compounds Polymerization Reactions with Organotin Compounds Unspecified Organotin Compounds
Commercial Application of Organotin Compounds
Symmetric Tetraorganolead Compounds Unsubstituted Tetraorganolead Compounds
Symmetric Tetraheterocyclic Lead Compounds Symmetric Unsaturated Tetraorganolead Compounds Functionally Substituted Symmetric Tetraorganolead
Compounds
XVII
470
474 474 476 477 477 477
482
489 492 493
494 496
499
504 508 508
509 515
515
519 529 530
530
2. 2.1 2.3 2.4 2.5 2.6 2.6.1 2.6.3 2.6.4 2.6.5 2.7 2.7.1 2.7.2
3.
4. 4.1 4.1.1 4.1.1.1 4.1.1.3 4.1.1.4 4.1.1.6 4.1.2 4.1.2.1 4.~.2.2
4.1.3 4.2 4.2.1 4.2.4 4.3 4.3.1 4.3.2 4.3.3 4.3.3.9 4.3.5 4.3.5.1 4.3.5.1.1
4.3.5.1.6.1
Unsymmetric Tetraorganolead Compounds Nonfunctional Tetraorganolead Compounds Heterocyclic Substituted Tetraorganolead Compounds Tetraorganolead Compounds with Olefinic Substituents Tetraorganolead Compounds with Acetylenic Substituents Functionally Substituted Tetraorganolead Compounds Tetraorganolead Compounds Containing Halogen Tetraorganolead Compounds Containing Oxygen Tetraorganolead Compounds Containing Sulfur Tetraorganolead Compounds Containing Nitrogen Metal-Substituted Tetraorganolead Compounds Bridged Tetraorganolead Compounds Tetraorganolead Compounds with Metallic Substituents
Organolead Hydrides
Organolead Compounds Containing Heteroatom-Lead Bonds Organolead Halides Triorganolead Halides Unsubstituted Triorganolead Halides Heterocyclic Triorganolead Halides Unsaturated Triorganolead Halides Functionally Substituted Triorganolead Halides Diorganolead Dihalides Unsubstituted Diorganolead Dihalides Substituted Diorganolead Dihalides Monoorganolead Halides Organolead Salts Organolead Pseudohalides Organolead Salts or Esters of Oxygen Acids Organolead Oxygen Compounds Organolead Oxides ~nd Hydroxides Organolead Peroxides Organolead Alkoxides Organolead Siloxanes Organolead Carboxylates Triorganolead Carboxylates Triorganolead Carboxylates Derived
Acids Triorganolead Carboxylates Derived
Acids Triorganolead Carboxylates Derived
Acids Triorganolead Carboxylates Derived
Substituted Acids Triorganolead Carboxylates Derived
Containing Acids Triorganolead Carboxylates Derived
Nitrogen-Substituted Acids
XVIII
from Unsubstituted
from Heterocyclic
from Unsaturated
from Functionally
from Halogen-
from Oxygen- and
532 536 536 536 541 541 541 541 541 547 547 550
550
551 551 552 557 557 557 558 559 561 562 562 562 563 566 566 570 571 571 572 572
573
573
573
573
573
573
4.3.5.2 4.3.5.2.1
4.3.5.3 4.4 4.5
5· 5·1 5.2
6. 6.1 6.5
7.
8. 8.1 8.2
BIBLIOGRAPHY
Diorganolead Carboxylates Diorganolead Carboxylates Derived from Unsubstituted
Acids Diorganolead Dicarboxylates Derived from Substituted
578
579
Acids 581 Monoorganolead Tricarboxylates 582 Organolead Compounds with Sulfur, Selenium, and Tellurium 584 Organolead Compounds with Nitrogen and Phosphorous 586
Organo-Polylead Compounds Hexaorganodilead Compounds 587 Organolead Compounds with Less Than Three Organic
Groups per Lead Atom
Bimetallic Organolead Compounds Organolead Derivatives of Groups I-IV Metals Organolead Derivatives with Transition Metal Coordina-
tion Compounds
Cyclic Organolead Compounds
Miscellaneous Organolead Compounds Polymerization Reactions with Organolead Compounds Unspecified Organolead Compounds
590
591
593
596
596 598
599
REVIEW PUBLICATIONS AND MONOGRAPHS 691
XIX
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