Acid-induced ring opening of α-bis(methylthio)methylenealkyl cyclopropyl ketones: a novel route to substituted cyclopentanones through carbocationic cyclizations

Patro, Balaram ; Deb, Biswajit ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1992) Acid-induced ring opening of α-bis(methylthio)methylenealkyl cyclopropyl ketones: a novel route to substituted cyclopentanones through carbocationic cyclizations Journal of Organic Chemistry, 57 (8). pp. 2257-2263. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00034a014

Related URL: http://dx.doi.org/10.1021/jo00034a014

Abstract

α-[Bis(methylthio)methylene]alkyl2-styrylcyclopropyl ketones lOa-d,f and their higher enyl analogues 10e,g undergo acid-induced ring opening and carbocationic cyclizations to afford substituted cyclopentanone derivatives. The structures of these products depend on the reaction conditions and the nature of the substituent in the aryl ring. The methodology has been extended to the synthesis of 11-oxosteroid precursors 22 and 25.

Item Type:Article
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