Tetrahedron

On the regioselectivity of coupling of substituted allyl radicals. Steric versus FMO control

DJ Pasto, G L'Hermine

Index: Pasto, Daniel J.; L'Hermine, Gael Tetrahedron, 1993 , vol. 49, # 16 p. 3259 - 3272

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Citation Number: 20

Abstract

The photo-induced decomposition of substituted-homoallylic 4-nitrobenzenesulfenates produces substituted allyl radicals which undergo dimerization and coupling with the 4- nitrobenzenethiyl radical. The regioselectivity of the dimerization of the allyl radicals is controlled by both steric and FMO properties depending on the nature of the substituent.