Acylation of aromatic substrates with ketenes. An example of vinyl oxocation reactivity

KR Fountain, P Heinze, M Sherwood…

Index: Fountain, K.R.; Heinze, Pamela; Sherwood, Mark; Maddex, Dave; Gerhardt, Greg Canadian Journal of Chemistry, 1980 , vol. 58, p. 1198 - 1205

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Citation Number: 5

Abstract

Acylations of aromatic substrates with ketenes involve the reactivity of species similar to vinyl cations. Resonance stabilization of ketene-aluminum chloride complexes seems to make these complexes less reactive than corresponding vinyl cations. The kinetic isotope effect of the reaction with dimethylketene and benzene is 1.06, compatible with vinylcation cases, but not with acylation with CH3COBF4 types of electrophiles. Substrate specificity was ...