Patro, Balaram ; Deb, Bishwajit ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1994) Rearrangement studies on 3,3-bis(methylthio)-1-(arylcyclopropyl) -2-propen-1-ols: synthesis of functionalized cyclopentenes and polyene esters Tetrahedron, 50 (1). pp. 255-264. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)80748-1
Abstract
The cyclopropyl carbinols 8 and 9 obtained by either borohydride reduction (or Grignard addition) of the cyclopropyl ketones 1 are shown to undergo acid induced ring opening and intramolecular cyclization (5-exo or 6-endo) or deprotonation to afford either cyclopentene, biphenyl or conjugated polyene derivatives depending on the nature of Lewis acid, reaction conditions and the structuralfeatures present in the cyclopropyl carbinol. A probable mechanism for the formation of various products has been suggested.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 15328 |
| Deposited On: | 13 Nov 2010 12:56 |
| Last Modified: | 22 Feb 2011 08:33 |
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