A simple route to derivatives of benzo[j]fluoranthene

Daniel J. Tate, Mohamed Abdelbasit, Colin A. Kilner, Helena J. Shepherd, Stuart L. Warriner, Richard J. Bushby

    Research output: Contribution to journalArticlepeer-review

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

    Keywords

    • Benzo[j]fluoranthene
    • Ferric chloride
    • Fluoranthene
    • Scholl reaction

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