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Communication | Regular issue | Vol 78, No. 2, 2009, pp.325-330
Published online, 16th October, 2008
DOI: 10.3987/COM-08-11550
Effect of a Metal Salt on Thiiranation of 2’-Adamantylidene-9-benzonorbornenylidene with 4,4’-Dithiodimorpholine and Acetic Anhydride

Yoshiaki Sugihara,* Hiroki Koyama, and Juzo Nakayama*

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


Using a solution of a metal salt, it was possible to decrease the quantity of Ac2O used in the thiiranation of 2’-adamantylidene-9-benzonorbornenylidene 1 with 4,4’-dithiodimorpholine 4 and Ac2O. Thiiranation in a 0.1 M Et2O solution of LiClO4 at -15 °C afforded thiiranes 2 and 3 in moderate yields without the decomposition of the thermally less stable 3.