The Journal of Organic Chemistry

2-Substituted acrylonitriles. 9. Reaction of 2-substituted acrylonitriles with diazoalkanes. Preparation of cyclopropanone cyanohydrins

A Oku, T Yokoyama, T Harada

Index: Oku, Akira; Yokoyama, Taka-aki; Harada, Toshiro Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5333 - 5337

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Abstract

The preparation of cyclopropanone cyanohydrins was investigated. The reaction of 2- acetoxyacrylonitrile (1) with carbenes, eg, diphenylcarbene, phenylcarbene, fluorenylidene, and methylene, gave the corresponding 1-acetoxy-1-cyanocyclopropanes (3). Similarly, the 1, 3-dipolar addition of 1 with diazoalkanes, eg, diphenyldiazomethane, phenyldiazomethane, diazofluorene, and 1-phenyldiazoethane, gave the corresponding ...

~30%

~67%

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~92%

~64%

~96%

~88%

~54%

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