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Issue 8, 1996
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Photochemical reactions of 1-naphthylamines and haloforms: formation of bis(4-amino-1-naphthyl)methylium salts with remarkably long-wave electronic absorption

Abstract

The photochemical colour change from colourless to green of N-substituted 1-naphthylamines 1a–c in CH2Cl2 containing a haloform was found to be irreversible, although optically active 3-(1-naphthylamino)camphor 1a had been reported to exhibit reversible photochromism in CHCl3. Irradiation of N-(cis-4-tert-butylcyclohexyl)-1-naphthylamine 1b with CHI3 in hexane gave bis-1,1′-[4,4′(N-cis-4-tert-butylcyclohexyl)aminonaphthyl]methylium triiodide as green needles and N-(cis-4-tert-butylcyclohexyl)-1-naphthylamine hydroiodide as colourless crystals. A plausible pathway for the photochemical reaction of the N-substituted 1-naphthylamines with a haloform, which is initiated by electron-transfer from the nitrogen in the amines to the haloform followed by radical reactions which liberate hydrogen halide, is proposed.

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Article type: Paper
DOI: 10.1039/P19960000789
J. Chem. Soc., Perkin Trans. 1, 1996, 789-792

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    Photochemical reactions of 1-naphthylamines and haloforms: formation of bis(4-amino-1-naphthyl)methylium salts with remarkably long-wave electronic absorption

    K. Maeda, Y. Horikoshi, M. Hayashi, Y. Mori and H. Nagano, J. Chem. Soc., Perkin Trans. 1, 1996, 789
    DOI: 10.1039/P19960000789

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