Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Regular issue | Vol 38, No. 8, 1994, pp.1733-1736
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6780
New Transformation of Lactam Sulfides to Tetrahydro-3,6-epithiobenzazocines via Bicyclic Sulfonium Salts with a Sulfonio Bridgehead

Tadashi Kataoka,*Yoshihide Nakamura, Harutoshi Matsumoto, Tetsuo Iwama, and Hiroshi Shimizu

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


Benzothiazinone (1) was chlorinated with N-chlorosuccinimide and subsequently submitted to [2++4] cycloaddition with 1,3-dienes in the presence of silver perchlorate to afford cyclic sulfonium salts (3). Reactions of 3 with sodium borohydride or sodium hydride provided 4-vinyltetrahydro-3,6-epithiobenzazocine derivatives (9) in good yields.