Reaction of 2,6-xylyl isoselenocyanate with organolithium compounds

Article abstract of DOI:10.1016/0040-4020(96)00707-7

Reaction of 2,6-xylyl isoselenocyanate (1) with organolithium compounds was examined focussing on the site selectivities. Phenyllithium attacked selenium exclusively whereas some benzylic organolithiums reacted at the central carbon of 1 to afford the corresponding lithium selenocarboximidates. Phenylethynyllithium and (t)BuLi gave mixtures of the carbophilic and selenophilic products. The lithium enolate of isobutyrophenone reacted with 1 at both its C- and O-nucleophilic centers attacking the central carbon of 1. By the alkylation of lithium selenocarboximidates formed from 1 and benzylic organolithiums, several selenoimidates were synthesized.