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 ...
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