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: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Special issue | Vol 15, No. 2, 1981, pp.807-814
Published online, 1st January, 1970
DOI: 10.3987/S-1981-02-0807
Cycloaddition of Benzothiazolium N-Phenacylide with Olefinic Dipolarophiles

Otohiko Tsuge,* Hiroshi Shimoharada, and Michiko Noguchi

*Graduate School of Engineering, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

Abstract

Benzothiazolium N-phenacylide, generated in situ from 3-phenacylbenzothiazolium bromide and triethylamine, reacted with maleic anhydride, N-(p-methoxyphenyl)maleimide, dimethyl maleate, and fumrate to give the corresponding tetrahydropyrrolo[2,1-b]benzothiazole derivatives, all of which were stable on treatment with triethylamine, in good yields respectively. With maleonitrile the sole cycloadduct was formed, whereas fumaronitrile gave a mixture of two stereoisomeric cycloadducts. In some cases, dimer and/or hydrated compound of ylide were formed as by-products. On treatment with triethylamine epimerization and ring-transformation of cycloadducts obtained from both the dinitriles were observed.