Radical Isomerization and Allylation Reactions of 2-Iodo-3,3-dimethyl-4-pentenoate Esters

Dennis P. Curran; Craig M. Jasperse; Ann C. Abraham

doi:10.1055/s-1992-21252

Synlett 1992; 1992(1): 25-26
DOI: 10.1055/s-1992-21252

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Radical Isomerization and Allylation Reactions of 2-Iodo-3,3-dimethyl-4-pentenoate Esters

Dennis P. Curran^* , Craig M. Jasperse, Ann C. Abraham

^*Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania,15260, USA

Abstract

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Sunlamp irradiation of methyl 2-iodo-3,3-dimethyl-4-pentenoate (2c) induces isomerization to an equilibrium mixture rich (13/1) in methyl 3-iodo-3-methyl-2-vinylbutanoate (3c). Allylations of 2c with allyl sulfides and stannanes produce mixtures of rearranged (9; 6-substituted 3-methoxycarbonyl-4,4-dimethyl-1,6-heptadienes) or unrearranged (8; 6-substituted 4-methoxycarbonyl-3,3-dimethyl-1,6- heptadienes) allylation products.

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