Tetrahedron

Generation of simple methylenecyclopropenes as reactive intermediates

WE Billups, AJ Blakeney, NA Rao, JD Buynak

Index: Billups, W. E.; Blakeney, Andrew J.; Rao, Nancy A.; Buynak, John D. Tetrahedron, 1981 , vol. 37, # 18 p. 3215 - 3220

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Citation Number: 16

Abstract

The dehydrochlorination of either 1, 2-dichloro-1-methylcyclopropane or 1-bromo-2-chloro-2- methylcyclopropane with potassium t-butoxide yields 2-t-butoxy-1-methylenecyclopropane. These results are interpreted in terms of methylenecyclopropene as a reactive intermediate which is trapped by addition of nucleophile (t-butoxide) to the cyclopropenyl double bond. The introduction of methanethiol to the reaction medium yields 2-thiomethyl-1- ...