Free-Radical Additions of Diselenides to Dimethyl Acetylenedicarboxylate, Methyl Propiolate, and Dimethyl Maleate

Article abstract of DOI:10.1021/jo00246a023

The photolysis of diphenyl or dimesityl diselenide with dimethyl acetylenedicarboxylate or methyl propiolate resulted principally in the formation of the corresponding vicinal bisselenides 1a,b,2a,b, and 6a,b via a free-radical chain addition mechanism.Dimethyl maleate underwent a selenyl radical mediated isomerization to dimethyl fumarate when similarly photolyzed with diphenyl diselenide.