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Dearomatisation of 1- and 2-cyanonaphthalene through nucleophilic conjugate addition

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
14
Identifiers
DOI: 10.1016/s0040-4039(02)00316-7
Keywords
  • Cyanonaphthalene
  • Dearomatisation
  • Dihydronaphthalenes
  • Conjugate Addition
  • Phosphine Borane Anions

Abstract

Abstract Conjugate nucleophilic addition of organolithium compounds to 1- and 2-cyanonaphthalene is described for the first time. The dearomatisation is carried out in the presence of HMPA and leads to functionalised dihydronaphthalenes. The nucleophiles used include simple lithium reagents as well as phosphorus-stabilised anions.

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