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Communication | Special issue | Vol 70, No. 1, 2006, pp.169-175
Published online, 7th November, 2006
DOI: 10.3987/COM-06-S(W)52
Investigation of Vinylcyclopropane Monoradical Cyclization-Fragmentation as a Possible Route towards Eight-Membered Rings

James A. Miranda* and R. Daniel Little

*Department of Chemistry, California State University, 6000 J Street, Sacramento, CA 95819-6057, U.S.A.

Abstract

A monoradical vinylcyclopropane cyclization-fragmentation route to eight-membered rings was investigated. 6-Exo-trig cyclization was preferred over the alternative 7-endo-trig cyclization, due to entropic factors and the position of a radical stabilizing electron withdrawing group. Changing position of the electron withdrawing group was not enough to entice 7-endo-trig cyclization.