Journal of Organic Chemistry p. 3972 - 3978 (1988)
Update date:2022-09-26
Topics:
Katritzky, Alan R.
Duell, Bradley L.
Durst, H. Dupont
Knier, Barry L.
2-Iodoso- and 2-iodoxybenzoic acids containing alkyl, alkyloxy, nitro, carboxyl, and water-solubilizing substituents have been synthesized, and their influence on the rates of hydrolysis of p-nitrophenyl diphenyl phosphate (PNPDPP), p-nitrophenyl isopropylphenylphosphinate (NPIPP), and p-nitrophenyl hexanoate (PNPH) has been determined in the presence of added cetyltrimethylammonium chloride (CTAC).All the compounds are true catalysts, with rates increasing with increasing catalyst concentration. 2-Iodoxybenzoic acids possess 60-110percent of the activity of their 2-iodosobenzoic acid analogues in 0.001 M CTAC.The effects of substituents of variable electronic and aqua/lipophilic character upon catalytic activity have been determined.Lipophilic substituents significantly enhanced the rates while simple ring substitution with electron-releasing and -withdrawing and water-soluble groups had only moderate effects.Extraordinary rate enhancements were obtained with 5-(2-hydroxyethoxy)-2-iodoxybenzoic acid and 5-(alkyloxy)-2-iodosobenzoic acid and -2-iodoxybenzoic acid derivatives, giving second-order rate constants of 400-5000 M-1 s-1.The efficient catalysis of the hydrolysis of active phosphorus derivatives renders these aromatic 2-iodoso- and 2-iodoxybenzoic acids potentially useful decontaminants.
View MoreZibo Linzi Darong Fine Chemical Co., Ltd(expird)
Contact:86-532-67773200; 15689126900
Address:Qidu town,Linzi district,Zibo city,Shandong province,China
Suzhou Time-chem Technologies Co., Ltd.
Contact:0512-63983931/68086856
Address:No. 1326 of Binhe Road, New District, Suzhou, Jiangsu, P. R. China
ClickChem Technology Co., Limited
Contact:+86-0310-6519966/0531-52893837
Address:No.750 Shunhua Road, High-Tech Zone, Jinan city, Shandong China
Nanjing Legend Pharmaceutical & Chemical Co., Ltd.
Contact:+86-25-83767696
Address:14-7 Zhongshan Lu Guluo District, Nanjing
Suzhou Sinosun Imp.&Exp. Corporation
website:http://www.szsinosun.com
Contact:+86-512-63488895,63488616
Address:No.758 East Jiangling Road Wujiang Economic & Technological Developmenty Zone Jiangsu China
Doi:10.1021/om00034a077
(1993)Doi:10.1007/BF00475657
(1987)Doi:10.1021/jo961699n
(1997)Doi:10.1016/S0040-4039(00)96151-3
(1987)Doi:10.1002/ejic.200700785
(2008)Doi:10.1002/anie.201108002
(2012)