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Communication | Regular issue | Vol 78, No. 2, 2009, pp.331-336
Published online, 16th October, 2008
DOI: 10.3987/COM-08-11551
Synthesis and Thermal Decomposition of Thiirane 1-Imides of 2’-Adamantylidene-9-benzonorbornenylidene

Yoshiaki Sugihara,* Ayumi Kobiki, and Juzo Nakayama*

*Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Shimo-okubo, Sakura-ku, Saitama 338-8570, Japan

Abstract

Two isolable thiirane 1-imides 21 and 22 were synthesized successfully by imination of anti- and syn-2’-adamantylidene-9-benzonorbornenylidene sulfides 19 and 20 with Chloramine T in CH2Cl2 and MeCN at -18 °C. Thermal decompositions of 21 and 22 in solution at room temperature or in the solid state on heating gave mainly 19, alkene 23, and aziridine 24.