• Sulphur isosters of carcinogenic hydrocarbons - Part II. 6∶12-Dimethylbenzo (1∶2-b, 5∶4-b′) dithionaphthene and thionaphtheno (4∶5∶4′∶5′) thionaphthene

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    • Keywords


      Phenanthrene; Stannous Chloride; Dimethyl Acetal; Hydriodic Acid; Phosphorus Pentachloride

    • Abstract


      With the view to study the significance of the 9∶10-phenanthrene double bond (“phenanthrene bridge”) in 9∶10-dimethyl-1∶2∶7∶8-dibenzanthracene (II), 6∶12-dimethylebenzo (1∶2b, 5∶4-b′)dithionaphthene (V) was prepared where both the phenanthrene bridges in (II) are removed by isosteric replacement with thiophene rings and themeso-positions are blocked by methyl groups. Compound (V) should prove noncarcinogenic.

      2∶7-Dimethoxyethylmercaptonaphthalene (IX) on cyclization gave thionaphtheno(4∶5∶4′:5′-)thionaphthene (VIII). The constitution (VIII) follows from the favoured α-cyclization in the naphthalene series and the similarity of its absorption spectrum with that of 3∶4-benzphenanthrene.

    • Author Affiliations


      V V Ghaisas1 K Rabindran1 B D Tilak1

      1. Department of Chemical Technology, University of Bombay, Bombay
    • Dates


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