1,2,2-tribromocyclopropanecarboxylic acid and derivatives - Valuable intermediates for four carbon cyclopropane and cyclopropene synthons


Aldulayymi A., Aldulayymi J., Baird M., Gerrard M., Koza G., Harkins S., ...More

TETRAHEDRON, vol.52, pp.3409-3424, 1996 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 52
  • Publication Date: 1996
  • Doi Number: 10.1016/0040-4020(95)01123-4
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.3409-3424

Abstract

Methyl 1,1,2-tribromocyclopropanecarboxylate is readily available by dibromocyclopropanation of methyl alpha-bromoacrylate. Reaction with methyllithium at low temperature provides a simple route to methyl 2-bromocyclopropene carboxylate. while modification of the ester group followed by reaction with methyllithium leads to a series of related four-carbon cyclopropenes. The tribromo-ester is also readily converted into 1,1,2,2-tetrabromocyclopropane, a valuable three-carbon cyclopropene synthon.