Electrochemical oxidation of acylsilanes and their tosylhydrazones

J Yoshida, M Itoh, S Matsunaga…

Index: Yoshida, Jun-ichi; Itoh, Masanori; Matsunaga, Shin-ichiro; Isoe, Sachihiko Journal of Organic Chemistry, 1992 , vol. 57, # 18 p. 4877 - 4882

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Citation Number: 32

Abstract

Oxidation potentials of acylsilanes were found to be much less positive than those of ketones an. d aldehydes. The effect of silicon is attributed to the rise of the HOMO level by the interaction between the C-Si u orbital and the nonbonding p orbital of the carbonyl oxygen which in turn favors the electron transfer. Preparative electrochemical oxidation of acylsilanes proceeded smoothly, giving rise to facile cleavage of the C-Si bond and the ...

~72%

~78%

~82%

~90%

~90%

~87%

~94%

~85%

~76%

~85%

~78%

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