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Selenium‐Containing Heterocycles From Isoselenocyanates: Synthesis of1,3‐Selenazolidine and Perhydro‐1,3‐selenazine Derivatives
Author(s) -
Sommen Geoffroy L.,
Linden Anthony,
Heimgartner Heinz
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500090
Subject(s) - chemistry , triethylamine , dichloromethane , aryl , alkyl , stereochemistry , selenium , organic chemistry , solvent
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)