Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Stereoselective Monoalkylation of α-Halocyclopropyllithiums. A Versatile Method for the Synthesis of α-Alkylcyclopropyl Acetates and Alkylidenecyclopropanes
Katuzi KitataniTamejiro HiyamaHitosi Nozaki
Author information

1977 Volume 50 Issue 12 Pages 3288-3294


The title carbenoids (7 and 8) prepared by the action of butyllithium on dihalocyclopropanes are smoothly methylated with methyl iodide. The product ratio of cis-methylated product (3)/trans-methylated one (4) (or endo-methylated product (5)/exo-methylated one (6) is found to depend on the aging period of the carbenoids; thermodynamic equilibration gives almost 3 or 5. This procedure has been extended to general alkylation by utilizing HMPA co-solvent. The resulting α-alkylated cyclopropyl halides are converted into allylic acetates or cyclopropyl acetates upon acetolysis and also into alkylidenecyclopropanes upon base treatment. The protonolysis of 8 gives trans- or exo-bromocyclopropanes stereoselectively.

Information related to the author

This article cannot obtain the latest cited-by information.

© The Chemical Society of Japan
Previous article Next article