Synthesis of 1,3-Oxaselenan-2-imines from Isoselenocyanates

Abstract

The reactions of aryl isoselenocyanates 1 with 3-chloropropan-1-ol (8) in the presence of sodium hydride in dichloromethane at room temperature gave 1,3-oxaselenan-2-imines 10 in fair yield. A reaction mechanism via nucleophilic attack of the alcoholate at the isoselenocyanate 1, followed by a 6-exo-tet cyclization, is most likely