Journal of Organic Chemistry p. 2681 - 2684 (1985)
Update date:2022-08-05
Topics:
Mazzocchi, Paul H.
Minamikawa, Saeko
Wilson, Paul
N-Methylphthalimide (NMP) undergoes a pair of competing photochemical reactions in the presence of alkenes.In one of these reactions the alkene adds to the C(O)-N bond of NMP in a concerted ?2 + ?2 process that ultimately leads to 2-benzazepine-1,5-diones (5).A competing electron-transfer process results in the formation of a radical cation-radical anion pair which can be efficiently trapped in alcohols solvents such as 4.The regiochemistry of these products is consistent with expectations for addition of an alcohol to a radical cation.Calculations usingthe Weller equation accurately predict when electron transfer should dominate the ?2 + ?2 process, when the ?2 + ?2 process should dominate the electron transfer process, and when the two should be directly competitive.Product studies on the formation of 4 and 5 for various alkenes in methanol solution are entirely consistent with this hypothesis.
View MoreContact:+86-15850770348
Address:51 OF XIANGFANGCUN ROAD, Nanjing 210002, China
Contact:+86-21-61318535
Address:Building 29,No.2139 Xizha Road, Fengxian District, Shanghai
Hangzhou TJM Chemical Trade Co., Ltd
Contact:86-571-88223276 86-13388481653
Address:2221#,Boyuexuan,1860# Binsheng Road,Binjiang District, Hangzhou CityZhejiang Province, 310051, P. R. China
Hebei DaPeng Pharm & Chem Co., Ltd.
Contact:86-317-7298678,0576-88861898 88861908
Address:West Songmen Village, East Songmen Town, Wuqiao, Cangzhou, Hebei ,China
Contact:86-571-86737118-8689
Address:No.69, 12 Street, HEDA, Hangzhou, Zhejiang, China
Doi:10.1016/0040-4020(96)00416-4
(1996)Doi:10.1002/ejoc.201901494
(2020)Doi:10.1021/ja00500a049
(1979)Doi:10.1016/S0968-0896(99)00204-7
(1999)Doi:10.1246/bcsj.52.156
(1979)Doi:10.1021/om0497893
(2004)