Journal of Organic Chemistry p. 4913 - 4918 (1993)
Update date:2022-08-03
Topics:
Getz, John J.
Prankerd, Richard J.
Sloan, Kenneth B.
Three series of O-imidomethyl derivatives of para-substituted phenolic compounds were synthesized and their rates of hydrolysis were studied.Saccharin, phthalimide, and succinimide served as the imide portions of the derivatives.Their rates of hydrolysis were found to be first order with respect to hydroxide from pH 7.0 to 10 or 11 and dependent on the acidity (leaving group potential) of both the imide and the phenol portions.The more acidic the imide or the phenol, the faster the rate of hydrolysis.However, the rates of hydrolysis were more sensitive to the acidity of the phenol.Trapping experiments with cyanide also suggested that the phenol anion was functioning as the leaving group in what is apparently an SN2 reaction.An amide derivative was found to hydrolyze more slowly than predicted from the analogous series and the pKa of the amide.This result is apparently due partially stereoelectronic constraints in the imide series that cause the CH2-O bond to be oriented more nearly perpendicular to the plane of the C(=O)N group and hence more accessible to nucleophilic attack.
View MoreShanghai PuYi Chem-Tech Co.,Ltd.
Contact:+86-21-57687505-227
Address:3 Floor, Building 11, No 201 MinYi Road, Songjiang District, Shanghai 201612, China
website:http://www.weichichem.com
Contact:+8613912949432
Address:Fine Chemical Industrial Base,Wujiang town,He County,Anhui China.
Wuhan Kemi-Works Chemical Co., Ltd
website:http://www.kemiworks.com
Contact:86-27-85736489
Address:Rm. 1503, No. 164, Jianghan North Rd., Wuhan, 430022 China
Contact:Tel: +86-25-58353800
Address:23 Lijing Road, Nanjing Hi-Tech Zone, Nanjing, Jiangsu, China, 210061
Contact:0833-5590788/5590338/5590055
Address:Victory in the town of Red Star Village,Mount Emei City,industrial concentration area storage processing logistics parkpark
Doi:10.1016/0223-5234(91)90207-4
(1991)Doi:10.1007/s10593-012-1036-9
(2012)Doi:10.1039/P29910000439
(1991)Doi:10.1002/mrc.1260290504
(1991)Doi:10.1021/ic50046a014
(1966)Doi:10.1016/j.tetasy.2012.01.010
(2012)