Radical Addition Reactions of 2-(Phenylseleno)propanedioates to Alkenes and Alkynes

Article abstract of DOI:10.1021/jo00064a023

Sunlamp photolysis of methyl or ethyl 2-(phenylseleno)propanedioate with a variety of alkenes and alkynes in benzene yielded addition products in good to excellent yields.The proposed mechanism involves a radical chain process in which addition of a malonate ester radical is followed by phenylseleno transfer.Monosubstituted alkenes, 1,1- and 1,2-disubstituted alkenes, terminal alkynes, and internal alkynes were shown to undergo this reaction.Addition to diallyl ether led to substituted tetrahydrofurans, characteristic of process involving initial addition, followed by cyclization prior to phenylseleno transfer.Vinyl arenes, conjugated dienes, and unsaturated carbonyl compounds proved unreactive.