Chiral organometallic reagents. Part XXIII. On the stereochemistry of the carbolithiation reaction of vinyl sulfides

Authors
Hoffmann, RW Koberstein, R Harms, K
Citation
Rw. Hoffmann et al., Chiral organometallic reagents. Part XXIII. On the stereochemistry of the carbolithiation reaction of vinyl sulfides, J CHEM S P2, (2), 1999, pp. 183-191
Citations number
68
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
ISSN journal
03009580 → ACNP
Issue
2
Year of publication
1999
Pages
183 - 191
Database
ISI
SICI code
0300-9580(199902):2<183:CORPXO>2.0.ZU;2-G
Abstract
The intramolecular carbolithiation of vinyl sulfides at -105 degrees C in T HF has been found to be stereospecific regarding the formation of the new c arbon-carbon bond and non stereospecific regarding the formation of the new carbon-lithium bond. The resulting alpha-durylthioalkyllithium compounds a re configurationally stable at -105 degrees C and epimerize at -90 degrees C.