Synthesis of Isolable Thiirane 1-Imides and Their Stereospecific Ring-enlargement to 1,2-Thiazetidines

The isolation of thiirane 1-imides was achieved via imination of anti- and syn-9,9′-bibenzonorbornenylidene sulfides by Chloramine T at room temperature, followed by crystallization of the reaction mixture at −18 °C. Allowing CD2Cl2 solutions of the thiirane 1-imides stand at room temperature or hea...

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Bibliographic Details
Published in:Chemistry letters 2008-06, Vol.37 (6), p.658-659
Main Authors: Sugihara, Yoshiaki, Aoyama, Yui, Okada, Haruki, Nakayama, Juzo
Format: Article
Language:English
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Summary:The isolation of thiirane 1-imides was achieved via imination of anti- and syn-9,9′-bibenzonorbornenylidene sulfides by Chloramine T at room temperature, followed by crystallization of the reaction mixture at −18 °C. Allowing CD2Cl2 solutions of the thiirane 1-imides stand at room temperature or heating their crystals to around 120 °C led to the formation of the corresponding 1,2-thiazetidines with retention of the configuration of the thiirane 1-imides.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2008.658