Synthesis of Hydroxamic Acids through -NOH Insertion of KetonesS. Bruce King, Wake Forest University

O

N

O

OHPh S

O

NH OH1.

2. Base, rt

O Table Results of –NOH insertion with cyclopentanone towards N-hydroxypiperidone synthesis

Entry Equivalent of PA

Base/Solvents Yield

1 0.9 2N NaOH / EtOH

18%

2 1.1 NaH / THF 10.6%

3 2 NaH / DMF trace

4 2 NaOMe / MeOH 33%

5 2 2N NaOH / EtOH

40%

6 4 2N NaOH / EtOH

44%

7 6 2N NaOH / EtOH

59%

8 10 2N NaOH / EtOH

69%

Crystal structure of N-hydroxypiperidone