REARRANGEMENT STUDIES ON BIS(METHYLTHIO)-1-(ARYLCYCLOPROPYL)-2-PROPEN-1-OLS - SYNTHESIS OF FUNCTIONALIZED CYCLOPENTENES AND POLYENE ESTERS

Authors
PATRO B DEB B ILA H JUNJAPPA H
Citation
B. Patro et al., REARRANGEMENT STUDIES ON BIS(METHYLTHIO)-1-(ARYLCYCLOPROPYL)-2-PROPEN-1-OLS - SYNTHESIS OF FUNCTIONALIZED CYCLOPENTENES AND POLYENE ESTERS, Tetrahedron, 50(1), 1994, pp. 255-264
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
1
Year of publication
1994
Pages
255 - 264
Database
ISI
SICI code
0040-4020(1994)50:1<255:RSOB>2.0.ZU;2-A
Abstract
The cyclopropyl carbinols 8 and 9 obtained by either borohydride reduc tion (or Grignard addition) of the cyclopropyl ketones 1 are shown to undergo acid induced ring opening and intramolecular cyclization (5-ex o or 6-endo) or deprotonation to afford either cyclopentene, biphenyl or conjugated polyene derivatives depending on the nature of Lewis aci d, reaction conditions and the structural features present in the cycl opropyl carbinol. A probable mechanism for the formation of various pr oducts has been suggested.