Alkyne migration in alkylidene carbenoid species: A new method of polyyne synthesis

S Eisler, N Chahal, R McDonald…

Index: Eisler, Sara; Chahal, Navjot; McDonald, Robert; Tykwinski, Rik R. Chemistry - A European Journal, 2003 , vol. 9, # 11 p. 2542 - 2550

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Citation Number: 72

Abstract

Abstract The synthesis of conjugated polyyne structures via a modification of the Fritsch– Buttenberg–Wiechell (FBW) rearrangement is reported. Our adaptation provides for the 1, 2- migration of an alkyne in a carbene/carbenoid intermediate that is conveniently effected via lithium–halogen exchange with the appropriate dibromo-olefinic precursor. This rearrangement is quite rapidly accomplished under mild conditions (hexane solution,− 78 ...