Convenient, rapid and highly regioselective cycloisomerisation of 4,4-disubstituted hepta-1,6-dienes employing neutral palladium chloride pro-catalysts

KL Bray, IJS Fairlamb, JP Kaiser, GC Lloyd-Jones, PA Slatford

Research output: Contribution to journalArticlepeer-review

Abstract

Optimum conditions for the cycloisomerisation of dimethyldiallylmalonate by complexes of the form [L2PdCl2] (L=RCN or DMSO) were found to be [(t-BuCN)(2)PdCl2] in 1,2-dichloroethane at 40degreesC. These conditions also allow the highly regioselective cycloisomerisation of a range of 4-substituted hepta-1,6-dienes to the corresponding 1-substituted 3,4-dimethylcyclopent-2-enes in good yield. However, substituents at the 4 position that are strongly coordinating inhibit the reaction.

Original languageEnglish
Article numberUNSP 1022-5528/02/0300-0049/0
Pages (from-to)49-59
Number of pages11
JournalTopics in catalysis
Volume19
Issue number1
Publication statusPublished - 2002

Keywords

  • palladium
  • cycloisomerisation
  • dienes
  • regioselectivity
  • kinetics
  • atom economy
  • PYRIDINE-OXAZOLINE COMPLEXES
  • C-BOND FORMATION
  • 1,6-DIENE CYCLOISOMERIZATION
  • EXO-METHYLENECYCLOPENTANES
  • FUNCTIONALIZED 1,6-DIENES
  • CYCLIZATION
  • CYCLIZATION/HYDROSILYLATION
  • ALPHA,OMEGA-DIENES
  • HETEROCYCLES
  • METATHESIS

Cite this