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.
View MoreJIANGXI AIFEIMU TECHNOLOGY CO.，LTD
Contact:+86-570-6040289
Address:FINECHEMICAL PARK,ZIBU TOWN,WANNIAN COUNTY,JIANGXI PROV.,CHINA,ZIP
Jiaozuo Zhongwen Trading Coporation Limited
Contact:--
Address:East Renmin Road
Contact:+86-021-58123769
Address:No.780 of Cailun Road,Zhangjiang Hi-tech Park,Pudong,Shanghai
Jinzhou Jiutai Pharmaceutical Co.,Ltd
Contact:+86-0416-5179890
Address:No.41, Taianli, Taihe District, Jinzhou, Liaoning
website:http://www.eastarchem.com/
Contact:1-800-898-2436
Address:1215 K Street, STE 1700
Doi:10.1021/jo01156a018
(1949)Doi:10.1021/jm00194a004
(1979)Doi:10.1002/anie.200904745
(2010)Doi:10.1021/jm00195a003
(1979)Doi:10.1021/jm00195a014
(1979)Doi:10.1039/b315817a
(2004)
