The Journal of Organic Chemistry

Synthesis of. gamma.-and. delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

MD Bachi, E Bosch

Index: Bachi, Mario D.; Bosch, Eric Journal of Organic Chemistry, 1992 , vol. 57, # 17 p. 4696 - 4705

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Citation Number: 66

Abstract

A general method for the synthesis of y-and &lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu, SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to ...