Vinyllithium reagents from arenesulfonylhydrazones

AR Chamberlin, JE Stemke…

Index: Chamberlin,A.R. et al. Journal of Organic Chemistry, 1978 , vol. 43, # 1 p. 147 - 154

Full Text: HTML

Citation Number: 190

Abstract

2, 4.6-Triisopropylbenzenesulfonylhydrazones of a wide range of ketones serve as a convenient source of vinyllith-ium reagents. Treatment with 2.0-3.0 equiv of alkyllithium reagent at-78" C in TMEDA-hexane followed by warming to 0" C rapidly generates the vinyl anions in most cases. The reagents so formed can be trapped with a variety of electrophiles. This procedure leads to a convenient synthesis of allylic alcohols. di-, tri-, and ...

Related Articles:

Reaction of 1-chloro-2-alkylcycloalkenes with organolithium reagents. A novel cyclopropanation reaction involving the generation of carbenes from vinyl halides

[Gassman,P.G.; Valcho,J.J.; Proehl,G.S. Journal of the American Chemical Society, 1980 , vol. 102, p. 6519]

Reaction of 1-chloro-2-alkylcycloalkenes with organolithium reagents. A novel cyclopropanation reaction involving the generation of carbenes from vinyl halides

[Gassman,P.G.; Valcho,J.J.; Proehl,G.S. Journal of the American Chemical Society, 1980 , vol. 102, p. 6519]

Generation and Reactions of Tetrasubstituted N??Lithiomethyl??succinimides

[Stemke,J.E. et al. Tetrahedron Letters, 1976 , p. 2947 - 2950]

More Articles...