A. Maercker et U. Girreser, POLYLITHIUMORGANIC COMPOUNDS .20. STEREOSELECTIVE SYNTHESIS OF VICINAL DILITHIOALKENES BY ADDITION OF LITHIUM METAL TO CARBON-CARBON TRIPLEBONDS, Tetrahedron, 50(27), 1994, pp. 8019-8034
The reaction of various cyclic and acyclic alkynes with lithium dust (
2% sodium) to form vicinal dilithioalkenes has been investigated: Alip
hatic alkynes, e.g. 5-hexyne (27a), exclusively afford the correspondi
ng (E)-dilithioalkenes, insoluble solids which ave stable at room temp
erature and allow access to a variety of tetrasubstituted olefins in a
cceptable yields.