132610-45-8Relevant articles and documents
Acid Catalyzed Ring Opening of β-Bis(methylthio)methylenealkyl Cyclopropyl Ketones: A Novel Approach to Substituted Cyclopentanones
Deb, Biswajit,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 2728 - 2758 (2007/10/02)
The bis(methylthio)methylenealkyl cyclopropyl ketones (2) undergo ring opening and subsequent cyclization in the presence of a variety of acid catalysts to give 3-arylcyclopentanone (3), 5-aryl-2-oxocyclopentanecarbothioates (4) and 2-bis(methylthio)methylene-3-arylcyclopentanones (5) in good yields.The open chain carbinols (9) and (10) could also be isolated under controlled conditions in few cases.The cyclization of (2) to cyclopentanone is shown to depend on aryl ring substituents.The mechanistic studies of this cyclization are consistent with the formation of benzyl cation (13) or cyclic oxonium ion intermediate (14).A propable mechanism involving these intermediates for the formation of all these products is suggested.