en
Scientific article
Letter
English

A Convenient Synthesis of Dibenzo[a,c]cyclooctene Based on Thioenol Ether Reduction

Published inTetrahedron Letters, vol. 34, no. 4, p. 639-642
Publication date1993
Abstract

9,10,11,12-Tetrahydrodibenzo[a,b]cyclooctane-9,12-diol (6) is found to be reluctant to double bond forming elimination. It gives a bridge ether (7) instead. The corresponding diketone (5) reacts with benzyl mercaptan to provide the bis-thioenol ether (8-a. The latter, upon treatment with Raney nickle, gives the desired title diene 1. An alternative approach to 1, based on repeated carbane addition to phenanthrene, is also presented.

Keywords
  • Intramolecular reductive coupling
  • Desulfurization of thioenol ethers
  • Axial chirality
  • Carbene addition
Funding
  • Swiss National Science Foundation - 20-32645.91
Citation (ISO format)
LOTTAZ, Pierre-André et al. A Convenient Synthesis of Dibenzo[a,c]cyclooctene Based on Thioenol Ether Reduction. In: Tetrahedron Letters, 1993, vol. 34, n° 4, p. 639–642. doi: 10.1016/S0040-4039(00)61640-4
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Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0040-4039
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