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Communication | Special issue | Vol 80, No. 2, 2010, pp.879-885
Published online, 16th September, 2009
DOI: 10.3987/COM-09-S(S)115
Novel Radical Cyclization Method Accompanied by Elimination of Hydrazyl Radical

Shoji Kobayashi, Hidefumi Hirao, Tatsuro Kawauchi, and Ilhyong Ryu*

*Department of Chemistry, Graduate School of Science, University of Osaka Prefecture, Sakai, Osaka 593-8531, Japan

Abstract

The potential of hydrazine group as the new radical leaving group was studied. Radical cyclization of (E)-1,1-dialkyl-2-(1-alkyloct-2-en-7-ynyl)hydrazines with n-Bu3SnH/AIBN, followed by protodestannylation, gave 1-alkenyl-2-methylenecyclopentanes, which arose by 5-exo cyclization and subsequent β-elimination of hydrazyl radical.