A novel sequence of radical rearrangements involving the 5-exo cyclisation of a 3-(methylenecyclopropyl) propyl radical

C Destabel, JD Kilburn

Index: Destabel, Christine; Kilburn, Jeremy D. Journal of the Chemical Society, Chemical Communications, 1992 , # 8 p. 596 - 598

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Citation Number: 13

Abstract

Radical 10, generated from the corresponding imidazolethiocarbonyl derivative 3 or the phenyl selenide 4, rearranges in a six-step process to give the cyclohexene 5, after reduction; this rearrangement sequence includes the selective 5-Exo cyclisation of a (methylenecyclopropyl) propyl radical and opening of the intermediate cyclopropylmethyl radical to give a ring-expanded product.