Novel Photochemical Synthesis of 5-Arylbenzo [b] chrysene Derivatives

Abstract

5-Arylbezo (b) chrysene-7, 12-diones (3a-d) were synthesized by the photochemical reaction of 2 bromo -3 -methoxy -1, 4-naphthoquinone (1) with 1-aryl-1-1'naphthylethylenes (2a-d) in 9-26% yields. The structure of these benzo [b] chrysene-7, 12-diones was determined from their spectral data and their chemical reactions. Reduction of 5-2'-naphthylbenzo [b] chrysene-7, 12-dione (3c) by lithium aluminum hydride gave 5-2'-naphthylbenzo [b] chrysene (5) in a yield of 74%. 7, 12-Diacetoxy-5-2'-naphthylbenzo [b] Ckhrysene-(6) was also obtained (64%) by the reductive acetylation of (3c).
All these benzo [b] chrysene derivatives have never been reported so far. The photochemical reaction might provide a new synthetic route to benzo [b] chrysene derivatives.