Journal of Organic Chemistry p. 1405 - 1409 (1985)
Update date:2022-08-11
Topics:
Perrin, Charles L.
Lollo, Charles Peter
Hahn, Chi-Sun
Soluble imidate anions, especially formimidate anions, HC(O-)=NR, can be prepared by treating the amide with NaH or KH in THF or Me2SO.N-Phenylformimidate anion can also be prepared in hydroxylic solvents by treating the amide with excess NaOH.The imidate anions have been characterized by proton NMR.The E stereoisomer is generally more stable than the Z, but the E/Z equilibrium constant is strongly solvent dependent.The results are compared with previous studies of base catalyzed proton exchange.According to saturation-transfer measurements, the barrier to nitrogen inversion in these imidate anions is 19-23 kcal/mol.The imidate anions could be protonated by trifluoroethanol to regenerate the amide as a nonequilibrium E/Z mixture, which then returned to equilibrium at a measurable rate.
View MoreJiangxi Lixin Pharmaceutical Co.,Ltd.
Contact:0798-8337222; 18979813215
Address:Jiangxi City, Jindezheng Province
Guangzhou Reachin Chemical Co., Ltd
Contact:+86-20-37087379 ext.604
Address:A122C-1, Tianyuan Plaza, 401 Tianyuan Rd., Tianhe, Guangzhou, China
Yibin Hope Pharmaceutical Co., Ltd.
Contact:+86-831-5109851 86-831-5109836
Address:Luolong Industrial Zone,Nanxi, Yibin City, Sichuan, China. | Email: wishmarketing@gmail.com | Website: http://www.hopepharma.cc/
Sichuan Highlight Fine Chemicals Co., Ltd.
Contact:+86-28-8525 1605
Address:A5-102 Airport base,388 West Airport Huang He Zhong Lu,2 Section
shanghai tuomiao chemicial co.,ltd.
website:https://www.tuomiaochem.com/
Contact:021 - 59853336
Address:shanghai
Doi:10.1039/c7ra06527b
(2017)Doi:10.1021/acs.joc.8b02712
(2019)Doi:10.1021/ac50067a026
(1929)Doi:10.1107/S0108270199002693
(1999)Doi:10.1071/CH9830895
(1983)Doi:10.3390/molecules24061113
(2019)