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 byphenylseleno transfer. Monosubstituted alenes, 1,1- and 1,2-disubstituted alkenes, terminal alkynes, and alkynes were shown to undergo this reaction. Addition to diallyl ether led to substituted tetrahydrofurans, characteristic of a process involving initial addition, followed by cyclization prior to phenylseleno transfer

Sunlamp photolysis of 2-(phenylseleno)propanedioates to alkenes and alkynes in benzene leads to good to excellent yields, with a proposed mechanism involving a radical chain process and phenylseleno transfer.

Paper

Radical addition reactions of 2-(phenylseleno)propanedioates to alkenes and alkynes

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