THE SYNTHESES OF 4B,5A-DIHYDRODIBENZ[3,4-5,6]ANTHRA[1,2-B]OXIRENE AND 4B,5A-DIHYDRO-5H-DIBENZ[3,4-5,6]ANTHRA[1,2-B]AZIRINE

The syntheses of the K-oxide and K-imine derivatives of dibenz[a,j]anthracene (1) are described. The parent hydrocarbon 1 that was obtained as a side product in the Elbs pyrolysis of (2-methyl-l-naphthyl)-1'-naphthylmethanone (10) was oxidized to 3-(2-formylphenyl)-3-phenanthrenecarboxaldehyde (3). Treatment of the dialdehyde with tris(dimethylamino)phosphine gave 4b,5a-dihydrodibenz[3,4:5,6]anthra[1,2-b]oxirene (4). Reaction of the oxirane with sodium azide followed by triethyl phosphite cyclization of the mixture of trans azido-alcohols so formed, yielded mainly 4b,5a-dihydrodibenz[3,4:5,6]anthra[1,2-b]azirine (5).