Download PDF
Synlett 1997; 1997(2): 167-168
DOI: 10.1055/s-1997-737
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Simple Entry to Fused N-Aryl 1,2-Thiazetidine-S-Oxides: Thermal Isomerisation to 1,4-Thiazine-S-Oxides and Nucleophilic Ring-Opening with Alcohols and Amines

Ronald N. Warrener* , Ananda S. Amarasekara
  • *Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, Australia, 4702, Fax: +61 79 30 9917; email: r.warrener@cqu.edu.au
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

We show that fused 1,2-thiazetidine-S-oxides can be produced in one step from readily available aryl sulfonylamines by cycloaddition with quadricyclane; these adducts undergo smooth rearrangement to fused 1,4-thiazines-S-oxides on heating, and can be ring-opened with alcohols to form cis-1,2-arylamino sulfinic esters and cis-1,2-arylamino sulfinamides on treatment with amines.

hetero Diels-Alder - sulfoxide configuration - photochemistry - norbornenes - quadricyclane cycloaddition