Studies in Phosphinemethylene Chemistry. XV. The Reaction of Tetraarylphosphonium Bromides with Vinylic Organolithium Reagents1

D Seyferth, J Fogel, JK Heeren

Index: Seyferth,D. et al. Journal of the American Chemical Society, 1966 , vol. 88, # 10 p. 2207 - 2212

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Citation Number: 22

Abstract

Abstract: The reaction of vinyllithium with tetraphenylphosphonium bromide was found to give styrene (65%) and triphenylphosphine (80%). Further studies suggested that these are formed via intermediate vinyltetraphenylphosphorane. When isopropenyllithium was used, amethylstyrene was produced in 70 yield, but analogous reactions of cis-and trans-1- propenyllithium gave only low yields of cis-and trans-propenylbenzene, respectively. The ...