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 30, No. 2, 1990, pp.753-758
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S81
Controlling Factors for the Formation of Pyrrole, Pyridine, and Azepine in Thermal Rearrangement of 2H-Azirines

Masumi Saruwatasi, Kazuaki Isonuma, and Hiroshi Taniguchi*

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

Abstract

Thermal rearrangement of 2-(cyclohexen-1-yl)- and 2-(cyclopenten-1-yl)-2H-azirines, bearing a methyl or a phenyl group at the 2-position of cycloalkenes, was compared with those of corresponding acyclic and benzofuranylazirines. Suppression of the cyclization into pyrrole in favor of pyridine and azepine formations from the azirines having cyclic unsaturation is explained by the strain of fused 2H-pyrrole and the electronic character of vinyl nitrene intermediates.