Stereoselectivity in Photocycloaddition of Bicyclic Enones to Olefins

Tobe Yoshito, Toshihiko Hoshino, Yukio Kawakami, Yasuo Sakai, Koji Kimura, Yoshinobu Odaira

研究成果: Article同行評審

17 引文 斯高帕斯(Scopus)

摘要

Stereoselectivity in photocycloaddition of bicyclic enones 1,2, 5, and 6 to 2-butene and cyclohexene is discussed. In the cases of 1 and 5, having a five-membered ring fused to the double bond of monocyclic enones, from two to four kinds of cycloadducts were always obtained regardless of the ring size of the enone moieties, and, therefore, stereoselectivity is relatively low. On the other hand, in the cases of 2 and 6, having a six-membered ring fused to the double bond of monocyclic enones, the formation of cis-anti-trans cycloadducts proceeded stereoselectively. This remarkable effect of fused ring size on stereoselectivity in photocycloaddition is ascribed to the degree of non-bonded hydrogen interaction in 1,4-diradical intermediates and can be associated with differing flexibility and rigidity of cyclohexane and cyclopentane rings.

原文English
頁(從 - 到)4334-4337
頁數4
期刊Journal of Organic Chemistry
43
發行號22
DOIs
出版狀態Published - 1 1月 1978

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