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Wittig reagents were successfully changed to symmetrical olefins when treated with elemental selenium. The reaction proceeds through a selenocarbonyl intermediate, which existence was confirmed by Diels-Alder reaction. Phosphonium ylides (1) have been widely utilized for the synthesis of olefins' and also known to react with sulfur to afford thiocarbonyl compounds.2 However, there is no report on the reaction of 1 with selenium. Recently, we found that the reaction of stable Wittig reagents (1) with episulfides afforded alkyl fumarates or maleates in good yields and this reaction might proceed through a thioaldehyde intermediate. 3
π SIMILAR VOLUMES
Ring-fused alkylidenecyclopropanes, bicyclo[n.1.0]alkylidene derivatives, were readily synthesized by olefination reaction of bicyclo[n.1.0]alkanone N,O-hemiacetals with Wittig reagents in good yields.