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Selenium-Containing Heterocycles From Isoselenocyanates: Synthesis of 1,3-Selenazolidine and Perhydro-1,3-selenazine Derivatives


Sommen, Geoffroy L; Linden, Anthony; Heimgartner, Heinz (2005). Selenium-Containing Heterocycles From Isoselenocyanates: Synthesis of 1,3-Selenazolidine and Perhydro-1,3-selenazine Derivatives. European Journal of Organic Chemistry, (14):3128-3137.

Abstract

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.

Abstract

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry, Organic Chemistry
Language:English
Date:2005
Deposited On:08 Oct 2012 14:41
Last Modified:24 Sep 2018 08:08
Publisher:Wiley-Blackwell
ISSN:1099-0690
Funders:Dr. Helmut Legerlotz-Foundation, Univeristät Zürich, F. Hoffmann-La Roche AG, Basel
OA Status:Green
Publisher DOI:https://doi.org/10.1002/ejoc.200500090
Related URLs:https://www.zora.uzh.ch/50684/

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