A simple route to derivatives of benzo[j]fluoranthene

Research output: Contribution to journalArticle

  • Authors:
  • Daniel J. Tate
  • Mohamed Abdelbasit
  • Colin A. Kilner
  • Helena J. Shepherd
  • Stuart L. Warriner
  • And 1 others
  • External authors:
  • Richard J. Bushby

Abstract

3,6,8,11-Tetramethoxybenzo[j]fluoranthene can be made from 1,6-dimethoxynaphthalene in a one-pot ferric chloride oxidation/methanol reduction procedure. The reaction is tolerant of the presence of substituents in the 7-position of the naphthalene nucleus and provides a quick and easy route to these particular benzo[j]fluoranthenes. The reactions presumably proceed through initial formation of a bond between the 4-positions of two naphthalene molecules followed by closure of the five-membered ring. Indeed in one case some 4,4′-binaphthyl was isolated from the reaction mixture and it was generally found that better yields of the benzo[j]fluoranthrenes were obtained starting from the 4,4′-binaphthyl rather than by using the naphthalene as the starting material. In an analogous manner to the ring-closure of the 4,4′-binaphthyls, starting from a hexakisalkoxyphenylnaphthalene, a hexakisalkoxyfluoranthene could be obtained. © 2013 Elsevier Ltd. All rights reserved.

Bibliographical metadata

Original languageEnglish
Pages (from-to)67-74
Number of pages7
JournalTetrahedron
Volume70
Issue number1
DOIs
StatePublished - 7 Jan 2014