Journal of the American Chemical Society p. 186 - 193 (1992)
Update date:2022-09-26
Topics:
Mahoney, Robert Patrick
Fretwell, Paul A.
Demirdji, Samuel H.
Mauldin III
Benson Jr., Olester
Koch, Tad H.
Bi(3,5,5-trimethyl-2-oxomorpholin-3-yl) (TM-3 dimer) undergoes bond homolysis to yield 3,5,5-trimethyl-2-oxomorpholin-3-yl (TM-3), which reduces propyldiquat (PDQ2+) to its radical cation PDQ+. The byproduct is 5,6-dihydro-3,5,5-trimethyl-1,4-oxazin-2-one (8). Similarly, bi(5,5-dimethyl-4-ethyl-2-oxomorpholin-3-yl) (DEM-3 dimer) cleaves to 5,5-dimethyl-4-ethyl-2-oxomorpholin-3-yl (DEM-3), which reduces paraquat (PQ2+) to its radical cation PQ+. The byproduct, 5,5-dimethyl-4-ethyl-3-methoxy-2-oxomorpholine (10), results from rapid addition of methanol solvent to the transient 5,6-dihydro-4-ethyl-5,5-dimethyl-1,4-oxazin-2-onium cation (11). Concentration versus time data for the respective viologen radical cations together with reduction potentials for the viologens place the reduction potentials for TM-3 dimer and DEM-3 dimer at -0.56 and -0.33 V versus NHE, respectively, in Tris/Tris·H+ buffered methanol. The kinetics of reduction are analyzed using numerical integration, and the two reducing agents are compared with dithionite.
View MoreZhengzhou Institute of Chiral Pharmer Research Co., Ltd.
Contact:86-371-55219111
Address:15 Floor, 2 Building, Central China Technovalley, Zhongyuan West Road
Beijing Zhongshuo Pharmaceutical T & D Co.,Ltd
Contact:0086-10-64430626
Address:ea No 16, HEPINGLI,DONGCHENG DISTRICT,BEIJING,P.R.CHINA.
Beijing Century Richap Chemistry Co.,Ltd
Contact:+86- 010-64455497
Address:Guannan County, Lianyungang City, Jiangsu Province, China
Fusilin chemical science & technology co., ltd.
Contact:532-80698166/86057573, +86-400-669-7885
Address:School of Material Science & Engineering, Shandong Uinversity of Science & Technology, Huangdao Zone, Qindao, Shandong
Cangzhou Senary Chemical Science-tech Co., Ltd
Contact:+86-317-3563899, 3563699
Address:168 Jinde Road, Cangzhou, Hebei, China
Doi:10.1021/jm4002988
(2013)Doi:10.1016/S0022-1139(00)81105-7
(1992)Doi:10.1039/c3cc42217h
(2013)Doi:10.1002/anie.200603740
(2007)Doi:10.1016/j.ejmech.2013.03.051
(2013)Doi:10.1021/ja01054a045
(1969)