CUMULATED TRIENEPHOSPHINE OXIDES - BIMOLECULAR TRAPPING OF AN ALKYLIDENECYCLOPROPYLIDENE

Authors
SANTELLIROUVIER C TOUPET L SANTELLI M
Citation
C. Santellirouvier et al., CUMULATED TRIENEPHOSPHINE OXIDES - BIMOLECULAR TRAPPING OF AN ALKYLIDENECYCLOPROPYLIDENE, Journal of organic chemistry, 62(26), 1997, pp. 9039-9047
Citations number
90
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
26
Year of publication
1997
Pages
9039 - 9047
Database
ISI
SICI code
0022-3263(1997)62:26<9039:CTO-BT>2.0.ZU;2-W
Abstract
Dihalocarbene addition to allenic phosphine oxides occurs mainly at th e allylic double bond. Treatment of dibromocarbene adducts with BuLi l eads to cumulated trienephosphine oxides. In some cases, the intermedi ate alkylidenecyclopropylidene (or its precursor) is exceptionally sta bilized, and this carbene (or carbenoid) is trapped by the correspondi ng cumulated trienephosphine oxide in a bimolecular process. The resul tant spiropentane is formed in a regio- and stereoselective manner.