Journal of the American Chemical Society p. 4684 - 4689 (1983)
Update date:2022-08-25
Topics:
Doi, Joyce Takahashi
Carpenter, Tracy Louise
Olmstead, Marylin M.
Musker, W. Kenneth
The synergistic effect of a Lewis acid (I2) and an intramolecular Lewis base facilitates the deacylation of thioesters.When iodine is added to aqueous slution of S-3-(dimethylamino)propylthioacetate (I), deacylation is accelerated by a factor of 103-104.A severafold acceleration is observed for S-2-(2-pyridyl)ethyl thioacetate (II), and no rate enhancement is observed in the reaction of S-n-butyl thioacetate (III).The rate of iodine consumption at invariant pH and thioseter and iodine concentrations is zero order in iodine when III reacts and the first order in iodine when I reacts.Both kinetic orders are observed when II reacts.The effect of pH and iodine concentration on the rates of I and II is explaned by an intramolecular interaction between an iodine-thioester complex and the neighboring amine.The product of the reaction of the unsubstituted thioester III is the disulfide.However, overoxidation is observed in the reactions of I and II, and the sulfonic acids were the isolated products.The product from the oxidation of I has been confirmed to be (CH3)2+NH(CH2)3SO3- (IV) by single-crystal X-ray crystallography.
View Morewebsite:http://www.angchenchem.com
Contact:+86-510-88302099 82327577
Address:Rm. 404/405, Floor 4th, No. 983 FengXiang Road, Wuxi, China
Contact:86 21 3772 9386
Address:Rm.1803,Starry Bldg.1,1505 Meijiabang Road,Shanghai 201620 China
Hangzhou Pharma & Chem Co.,Ltd.
Contact:+86-571-87040515
Address:No,139Qingchun Rd
Contact:+49-4101-3053-0
Address:Waldhofstrasse 14 ,25474 Ellerbek Germany
Hunan Dinuo Pharmaceutical Co.,Ltd.
Contact:86-731-88280100*8561
Address:Bio-pharmaceutical industrial park, Liuyang, Hunan, China
Doi:10.1246/bcsj.43.1530
(1970)Doi:10.1039/c4dt02474e
(2015)Doi:10.1016/j.carres.2016.11.009
(2017)Doi:10.1039/c5cc01378j
(2015)Doi:10.1021/ja01148a546
(1951)Doi:10.1007/s10870-008-9471-2
(2009)