Journal of the American Chemical Society p. 1476 - 1480 (1984)
Update date:2022-08-04
Topics:
Wagner, William R.
Spero, Denice M.
Rastetter, William H.
The ability of several aryloxaziridines to transfer an oxygen atom to phenolates was examined. 2-(p-Nitrophenyl)-3-tert-butyloxaziridine (1) was found to oxidize potassium 2,6-dialkylphenolates to the corresponding p-benzoquinones.Product studies and an observed ESR signal suggest an electron-transfer mechanism for these oxidations. 18O-labeled oxaziridine 30 was prepared.Oxidations of phenolates with 30 rigorously establish the oxaziridine ring oxygen as the atom that is transferred to substrate.Kinetic studies with oxaziridine 1 and the isomeric nitrone 15 rule out the nitrone as an obligate intermediate in the oxygen-transfer reaction.In the oxidation of substrate, a single electron transfer from phenolate to oxaziridine is thought to generate a phenoxy/nitroxyl radical pair, which upon coupling and fragmentation achieves the oxygen transfer.These oxygen-transfer reactions serve as models for the proposed flavin-based oxaziridine 34 in enzyme-mediated monooxygenations.
View MoreQINGDAO NEW FLOURISH INTERNATIOANAL TRADE CO., LTD.
Contact:+86 532 80861829
Address:No. 1, Yinchuan East Road, 266061, Qingdao, China
Beijing Stable Chemcial Co.ltd
Contact:86-10-63785052
Address:A1301 Technological Edifice. No.4 FuFeng Road,FengTai District, Beijing. China
Anhui Qingyun Pharmaceutical and Chemical Co.,Ltd
Contact:+86-551-63633067
Address:Shuangfeng Road Hefei Anhui
Chengdu ZY Biochemical Technology Co., LTD
Contact:0086-28-88680086
Address:170 Qingpu Road, Shouan Town, Pujiang County
zhenjiang runjing high purity chemical co ltd
Contact:+86-511-83361155
Address:No.8.haixi road,international chemical park
Doi:10.1080/14756366.2017.1344236
(2017)Doi:10.1021/ol501271v
(2014)Doi:10.1002/chem.200500994
(2006)Doi:10.1039/c39910001156
(1991)Doi:10.1016/0039-128X(83)90089-2
(1983)Doi:10.1016/j.bmc.2005.12.020
(2006)