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A novel photorearrangement of 7,12-dimethylbenz(a)anthracene-7,12-epidioxide into 6b,11b-dihydro-6b,11b-dimethyl-benzofuro[3,2-b]naphtho[1,2-d]furan

✍ Scribed by Mahendra K. Logani; Willodene A. Austin; Ronald E. Davies

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 217 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85319-3

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✦ Synopsis

In a previous communicationl, we reported the formation of a novel bicyclic acetal, 1, in the photolysis of 7,12-dimethylbenz(a)anthracene (DMBA, 2). This report describes the structural elucidation of another photolysis product, 3, of this hydrocarbon, obtained [8X, mp 168 -172" (dec.)] by direct irradiation (filtered xenon arc, 295-400 nm) of 2 in hexane or benzene (0.33% solution) in a Pyrex container for 1 h. The product was separated and isolated by TLC (silica gel, hexane/benzene/methanol 30:70:1, Rf 0.68. By high resolution mass spectrometry2 the molecular composition of 2 was established as C20H1602 (m/e 288.1161; Calcd. 288.1150; error, 3.8 ppm). The principal fragment ions were observed at m/e 273 (41.4%) and 245 (18.7%). The IR exhibited no signals corresponding to OH or 00 functions. The NMR3 (CS2) displayed the following signals: s 1.77 (CH3, s), 1.81 (CH3, s),

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