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Issue 4, 1993
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Synthesis and spontaneous racemization of benz[a]anthracene 3,4-oxide: photochemical oxygen-walk rearrangements of arene oxides of benz[a]anthracene and triphenylene to yield oxepines

Derek R. Boyd,  Narain D. Sharma,  Shiv K. Agarwal,  Guru S. Gadaginamath,  Gerard A. O'Kane,  W. Brian Jennings,  Haruhiko Yagi  and  Donald M. Jerina 

Abstract

Benz[a]anthracene 3,4-oxide 2, when synthesised from optically pure dibromo ester precursors, was found to have racemized spontaneously and was accompanied by anthra[2,1-b]oxepine 14. Photoisomerization of benz[a]anthracene 3,4-oxide 2, triphenylene 1,2-oxide 4 and benz[a]anthracene 1,2-oxide 5 proceeds via an oxygen-walk mechanism to yield anthra[2,1-b]oxepine 14, phenanthro[10,9-b]oxepine 16 and anthra[2,1-f]oxepine 17 respectively.

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Article type: Paper
DOI: 10.1039/P19930000423
Citation: J. Chem. Soc., Perkin Trans. 1, 1993,0, 423-429
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    Synthesis and spontaneous racemization of benz[a]anthracene 3,4-oxide: photochemical oxygen-walk rearrangements of arene oxides of benz[a]anthracene and triphenylene to yield oxepines

    D. R. Boyd, N. D. Sharma, S. K. Agarwal, G. S. Gadaginamath, G. A. O'Kane, W. B. Jennings, H. Yagi and D. M. Jerina, J. Chem. Soc., Perkin Trans. 1, 1993, 0, 423
    DOI: 10.1039/P19930000423

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