Acid catalyzed ring opening of α-bis(methylthio)methylenealkyl cyclopropyl ketones: an intramolecular alkylation approach to substituted cyclopentanones

Deb, B. ; Asokan, C. V. ; Ila, H. ; Junjappa, H. (1988) Acid catalyzed ring opening of α-bis(methylthio)methylenealkyl cyclopropyl ketones: an intramolecular alkylation approach to substituted cyclopentanones Tetrahedron Letters, 29 (17). pp. 2111-2114. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4039(00)87848-X

Abstract

α-Bis(methylthio)methylenealkyl cyclopropyl ketones 4̲ , prepared by the addition of dimethyloxosulphonium methylide to the respective α-cinnamoylketene dithioacetals 3̲, undergo facile acid catalyzed intramolecular cyclization with participation of bis(methylthio)methylene double bond to give substituted cyclopentanones 5a̲-d̲ and 6a̲-e̲ in good yields.

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