BOYD, DR,SHARMA, ND,AGARWAL, SK,GADAGINAMATH, GS,OKANE, GA,JENNINGS, WB,YAGI, H,JERINA, DM;

1993

February

Rna-A Publication of The Rna Society

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

Validated

()

ABSOLUTE STEREOCHEMISTRY THEORETICAL PREDICTIONS METABOLITES 1,2-OXIDE

423

429

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-oxide2, triphenylene 1,2-oxide4 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.