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Selenium-Containing Heterocycles From Isoselenocyanates: Synthesis of1,3-Selenazolidine and Perhydro-1,3-selenazine Derivatives

✍ Scribed by Geoffroy L. Sommen; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
179 KB
Volume
2005
Category
Article
ISSN
1434-193X

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✦ Synopsis

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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Selenium-Containing Heterocycles from Is
Selenium-Containing Heterocycles from Isoselenocyanates: Synthesis of 1,3-Selenazinane and 1,3-Selenazinanone Derivatives
✍ Geoffroy L. Sommen; Anthony Linden; Heinz Heimgartner 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 German ⚖ 174 KB 👁 1 views

## Abstract The reaction of the intermediate ketene N,Se‐hemiacetal **3**, prepared from cyanomethylene derivatives **1** by treatment with Et~3~N and aryl isoselenocyanates **2**, with bis‐electrophiles **6, 7, 9**, and **11** in DMF affords tetrahydro‐1__H__‐1,3‐selenazine (=1,3‐selenazinane) der