Cyanation of alcohols with diethyl cyanophosphonate and 2, 6-dimethyl-1, 4-benzoquinone by a new type of oxidation-reduction condensation

…, T Minowa, Y Hagiwara, T Mukaiyama

Index: Masutani, Kouta; Minowa, Tomofumi; Hagiwara, Yoshiaki; Mukaiyama, Teruaki Bulletin of the Chemical Society of Japan, 2006 , vol. 79, # 7 p. 1106 - 1117

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Citation Number: 19

Abstract

Cyanation of various alcohols by a new type of oxidation–reduction condensation is described. Primary alkyl diphenylphosphinites, 2, 6-dimethyl-1, 4-benzoquinone (DMBQ), and diethyl cyanophosphonate gave the corresponding nitriles in high yields. During the above experiment on cyanation of 4-phenylbutan-2-ol, the unexpected formation of a mixture of nitrile and isocyanide was observed. After careful examination of the reaction ...

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