Journal of the Chemical Society. Perkin transactions II p. 923 - 930 (1986)
Update date:2022-08-04
Topics:
Durham, Dana
Kingsbury, Charles A.
The stereochemistry and kinetics of acid-catalysed ring-opening reactions of epoxides are reported.Predominant inversion is found in the usual hydroxylic solvents.As the nucleophilicity of the solvent diminishes and acidity increases, the stereochemistry changes to predominant retention.Electron-donating substituents also tend to favour retention.In mixed solvents, the solvent microstructure is altered, leading to net retention for nucleophiles such as methanol.The exception is dioxane-methanol, which gives enhanced inversion.Molecular mechanics calculations indicate an electrostatic preference for the retention route, but a steric preference for inversion.The activation parameters indicate a negative entropy for both inversion and retention paths.Possible reasons are discussed for the entropy of the retention route being in the range normally found for A2 reactions.
View MorePuyang Huicheng Electronic Material Co., Ltd
website:http://huichengchem.weba.testwebsite.cn/index_en.html
Contact:+86-393-8910800
Address:West Section Shengli Road, Puyang457000, China
Jiangsu Willing Bio-Tech Co ltd
website:http://www.willingbio.com/
Contact:+86 18796908173
Address:No 18 Guoqiao Road
Contact:+86-579-85206992
Address:No 451 chouzhou north road ,room 1106 int'l business center , yiwu ,china
Yangling Ciyuan biotech Co., Ltd.
Contact:86-15802970736
Address:2-1804, International Park Mansion, No.2, South Fengdeng Road, Lianhu District
Chongqing Werlchem Fine Chemical Co. Ltd
Contact:+86-23-67521957
Address:NO.15,Fortune Road,Yubei District,401121,Chongqing,China
Doi:10.1002/adsc.201801305
(2019)Doi:10.1016/S0040-4039(00)82137-1
(1988)Doi:10.1021/ic1000842
(2010)Doi:10.1021/ol016707n
(2001)Doi:10.1021/jo101501u
(2010)Doi:10.1016/j.carres.2019.03.006
(2019)
