アミン-N-オキシドの関与する反応(第8報) : 第2級アルコールの酸化

概要

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Secondary alcohols and hydroxycarboxylic esters were reacted with the oxygen in pyridine 1-oxide (I), using a catalyst, to obtain the corresponding ketones and ketocarboxylic acid esters ; R-CH (OH)-COOEt (A), R-CH (OH)-CO-R'(B), and R-(CH_2)_n-CH (OH)-(CH_2)_n-R'(n=0,1) (C). In the A type, with R=phenyl, using R-C_0,13% of ethyl benzoyl-formate was obtained, while with R=CH_3,10% of paraldehyde was obtained. In the B type, platinated palladium-carbon catalyst was used and, in the case of R=R'=phenyl, dibenzoyl was formed quantitatively, while with R=CH_3,only a trace of the objective compound was obtained. The same reaction can be carried out on triethylamine N-oxide under a milder condition than that for I. In the C type, using platinated palladium-carbon catalyst, the ketone was formed in a high yield when R and/or R'was phenyl but the yield decreased with introduction of a methylene group. When diphenylcarbinol was used, absence of I resulted in disproportionation reaction.
社団法人日本薬学会の論文
1977-05-25