Journal of the Chemical Society. Perkin transactions I p. 1461 - 1466 (1996)
Update date:2022-08-05
Topics:
Moriwaki, Hiroshi
Matsumoto, Takashi
Nagai, Toshikazu
Oshima, Takumi
The photoreactions of diphenylhomobenzoquinones 1a-d bearing 2-bromo and 2-methyl substituents have been investigated in the presence of amine donors. The products of these reactions are much dependent on the substituents and the nature of added amines. Irradiation of 1-bromo substituted diphenylhomobenzoquinone 1a with triethylamine (TEA) resulted in ring-opening of the fused-cyclopropane moiety to give 2-diphenylmethyl- 1,4-benzoquinone 3a. However, the photoreaction of 1a with N,N-dimethylaniline (DMA) yielded the 1:1 animated bicyclic dione 4a and bis(p-dimethylamino-phenyl)methane 7 along with 3a. In contrast, irradiation of 1-methyl substituted diphenylhomobenzoquinones 1b-d with TEA brought about hydrogenation of the C=C double bond to give the bicyclic diones 8b-d. Similar photoreaction of 1b,c with DMA provided only the 1:1 animated bicyclic diones 4b,c, although the trimethyl substituted 1d remained essentially intact.
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