Summary
4:5-Benzothionaphthene (II) was obtained by theα-cyclization ofβ-naphthylω-dimethoxyethyl sulphide (I), and the hitherto unknown naphtho-(1′:8′-bc)-thiapyran (IV) by theperi-cyclization ofα-naphthylω-dimethoxyethyl sulphide (III).
Naphthalene-1:5-dithiol was obtained in 85% yield by an improved method. Condensation of naphthalene-1:5 and 2:6-dithiols with two molecules of bromoacetaldehyde dimethyl acetal gave (VIII) and (XI). The former cyclized in theperi-positions to give “1:6-thiapyrene” (IX) which was orange in colour, and the latter cyclized in theα-positions to give 4:5, 5′:4′-dithionaphthene (XII), an isoster of chrysene which was colourless. Chrysene and (XII) gave similar absorption spectra, which were markedly different from the absorption spectrum of (IX).
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Communicated by Dr. K. Venkataraman,f.a.sc.
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Tilak, B.D. A new synthesis of thiophenes and thiapyrans. Proc. Indian Acad. Sci. (Math. Sci.) 33, 71 (1951). https://doi.org/10.1007/BF03172185
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DOI: https://doi.org/10.1007/BF03172185