Issue 10, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

U. K. Syam Kumar,a   Pranab K. Patra,a   Hiriyakkanavar Ila,*a   Hiriyakkanavar Junjappa*a  and  Parimal K. Bharadwaja  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology, Kanpur, U.P., India.
E-mail: hila@iitk.ac.in
Fax: ; Fax: 91-512-590007, 91-512-590260

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.

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Article information

DOI
https://doi.org/10.1039/B001043J
Article type
Paper
Submitted
07 Feb 2000
Accepted
22 Mar 2000
First published
28 Apr 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1547-1550

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

U. K. S. Kumar, P. K. Patra, H. Ila, H. Junjappa and P. K. Bharadwaj, J. Chem. Soc., Perkin Trans. 1, 2000, 1547 DOI: 10.1039/B001043J

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