Cyanoketenes. Cycloadditions of halocyanoketenes to benzaldehydes

HW Moore, F Mercer, D Kunert…

Index: Moore,H.W. et al. Journal of the American Chemical Society, 1979 , vol. 101, p. 5435 - 5436

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Citation Number: 17

Abstract

then suffer stereospecific decarboxylation under the reaction conditions to give the alkenes. Even though this stereoselective conversion of an aldehyde into an alkene is of synthetic note, it does not constitute the most significant aspect of this work. Most important is the fact that the initial cycloaddition is a nonconcerted dipolar process in which the cyanoketene uniquely functions as an electrophile and the aldehyde as the nucleophile (zwitterion 1, ...