Noboru Sonoda

Reaction of 2,6-xylyl isoselenocyanate with organolithium compounds

Abstract Reaction of 2,6-xylyl isoselenocyanate ( 1 ) with organolithium compounds was examined focussing on the siteselectivities. 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.

STANNYLFORMYLATION OF VINYLCYCLOPROPANES ACCOMPANIED BY RADICAL RING-OPENING

Abstract Treatment of vinylcyclopropanes with CO in the presence of Bu 3 SnH and AIBN (catalytic) leads to a stannylformylated product via a cyclopropylcarbinyl radical opening to a homoallylic radical.