Treatment of ω-halo alkylamines 9 and 10 with aryl and alkyl
isoselenocyanates 6a–g in the presence of triethylamine in
dichloromethane gave the corresponding 1,3-selenazolidines
11a–g and perhydro-1,3-selenazines 12a–g, respectively, in
good to excellent yields. Chemical and spectroscopic evidence
for the structures of all new compounds are presented, and in selected examples the molecular structures have been established by X-ray crystallography. The analogous reactions with isothiocyanates have been used for the preparation
of 1,3-thiazolidines and perhydro-1,3-thiazines.