SYNTHESIS, SPONTANEOUS RACEMIZATION AND PHOTOISOMERIZATIONOF BENZOPYRENE 9,10-OXIDE

DOI: 10.1039/P19880003013

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 3013 - 3018 (1988)

Update date:2022-07-30

Topics:

Authors:

Agarwal, Shiv K.

Boyd, Derek R.

Dunlop, Robert

Jennings, W. Brian

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Article abstract of DOI:10.1039/P19880003013

Benzopyrene 9,10-oxide (4) and the isomeric pyreno<4,5-b>oxepine have been simultaneously santhesyized from racemic and optically active bromo acetate precursors of known absolute configurations.Spontaneous thermal racemisation of benzopyrene 9,10-oxide (4) , and readily occuring photoisomerization of this arene oxide oxepine (9)> occur as predicated from PMO calculations of resonance energy changes associated with these pericyclic reactions.Optically pure samples of the mammalian metabolites 9,10-epoxy-(12) and trans--9,10-dihydroxy-9,10,11,12-tetrahydrobenzopyrene (13) have been obtained.

Full text of DOI:10.1039/P19880003013

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