Al. Braga et al., STEREOCONSERVATIVE FORMATION AND REACTIVITY OF ALPHA-CHALCOGEN-FUNCTIONALIZED VINYLLITHIUM COMPOUNDS FROM ALPHA-BROMO-VINYLIC CHALCOGENIDES, Synlett, (5), 1997, pp. 595
Bromine/lithium exchange was performed upon treatment of alpha-bromo-v
inylic chalcogenides with butyllithium in hexane at room temperature t
o provide alpha-chalcogen-vinyllithium intermediates quantitatively. A
ddition of electrophiles to the lithiated compounds gave the correspon
ding functionalized vinylic chalcogenides in good yields with retentio
n of configuration.