Lewis acid-induced rearrangment of α-[bis(methylthio)methylene]ethyl-2-styrylcyclopropylcarbinols: unexpected formation of a novel bicyclo[3.2.1]octadiene framework

Syam Kumar, U. K. ; Patra, Pranab K. ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar ; Bharadwaj, Parimal K. (2000) Lewis acid-induced rearrangment of α-[bis(methylthio)methylene]ethyl-2-styrylcyclopropylcarbinols: unexpected formation of a novel bicyclo[3.2.1]octadiene framework Journal of the Chemical Society, Perkin transactions 1 (10). pp. 1547-1550. ISSN 1472-7781

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Official URL: http://www.rsc.org/Publishing/Journals/P1/article....

Related URL: http://dx.doi.org/10.1039/b001043j

Abstract

The α-[bis(methylthio)methylene]ethyl-2-styrylcyclopropylcarbinols 9a-c undergo a simple but unexpected skeletal rearrangement in the presence of stannic chloride in nitromethane to afford bicyclo[3.2.1]octadiene derivatives 10a-c exclusively in good yields. The structure of 10a was conclusively elucidated by X-ray diffraction studies. A possible mechanism governing the formation of 10 is proposed.

Item Type:	Article
Source:	Copyright of this article belongs to Royal Society of Chemistry.
ID Code:	4572
Deposited On:	18 Oct 2010 07:29
Last Modified:	16 May 2016 15:12

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