Chiral organometallic reagents. Part XXV. The stereochemistry of the ring opening of cyclopropylallyllithium compounds

Authors
Hoffmann, RW Koberstein, R
Citation
Rw. Hoffmann et R. Koberstein, Chiral organometallic reagents. Part XXV. The stereochemistry of the ring opening of cyclopropylallyllithium compounds, J CHEM S P2, (3), 2000, pp. 595-602
Citations number
35
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
ISSN journal
03009580 → ACNP
Issue
3
Year of publication
2000
Pages
595 - 602
Database
ISI
SICI code
0300-9580(2000):3<595:CORPXT>2.0.ZU;2-M
Abstract
The ring opening of the cyclopropylallyllithium compounds 19 and 34 to give the alpha-durylhomoallyllithium compounds 20 has been shown to proceed at -107 degrees C with greater than or equal to 90% of stereochemical purity. The resulting alpha-durylthioalkyllithium compounds are configurationally s table at that temperature. They racemize at -78 degrees C with a half life of 90 min.