Domino Friedel–Crafts??Type Cyclizations of Difluoroalkenes Promoted by the α??Cation??Stabilizing Effect of Fluorine: An Efficient Method for Synthesizing Angular …

K Fuchibe, H Jyono, M Fujiwara, T Kudo…

Index: Fuchibe, Kohei; Jyono, Hideharu; Fujiwara, Masaki; Kudo, Takao; Yokota, Misaki; Ichikawa, Junji Chemistry - A European Journal, 2011 , vol. 17, # 43 p. 12175 - 12185

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Citation Number: 32

Abstract

Abstract In order to synthesize polycyclic aromatic hydrocarbons with nonlinear arrangements (angular PAHs), acid-promoted domino cyclizations of 1, 1-difluoroalk-1-enes and 1, 1-difluoroalka-1, 3-dienes were studied. 1, 1-Difluoroalkenes, each bearing two aryl substituents, were regioselectively protonated with FSO 3 H⋅ SbF 5 to generate fluorine- stabilized carbocations, which readily underwent domino Friedel–Crafts-type cyclizations ...