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

Authors
Kumar, UKS Patra, PK Ila, H Junjappa, H Bharadwaj, PK
Citation
Uks. Kumar et al., Lewis acid-induced rearrangment of alpha-[bis(methylthio)methylene]ethyl-2-styrylcyclopropylcarbinols: unexpected formation of a novel bicyclo[3.2.1]octadiene framework, J CHEM S P1, 10, 2000, pp. 1547-1550
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Volume
10
Year of publication
2000
Pages
1547 - 1550
Database
ISI
SICI code
0300-922X(2000)10:<1547:LAROA>2.0.ZU;2-L
Abstract
The alpha-[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 derivati ves 10a-c exclusively in good yields. The structure of 10a was conclusively elucidated by X-ray diffraction studies. A possible mechanism governing th e formation of 10 is proposed.