Journal of the American Chemical Society p. 5240 - 5244 (1990)
Update date:2022-08-11
Topics:
Dietze, Paul E.
Wojciechowski, Marek
It is shown that during the trifluoroethanolysis of 2-butyl 4-bromobenzenesulfonate, containing 18O in the nonbridging oxygens, scrambling of the oxygen label occurs. When enantiomerically enriched 2-butyl 4-bromobenzenesulfonate is subjected to the same solvolysis conditions, racemization of the starting ester is not observed. Therefore if an ion-pair intermediate is involved in the trifluoroethanolysis reaction, the ion pair has a sufficient lifetime to permit rotation of the anion leading to oxygen scrambling. However, rotation of the cation, which would lead to racemization, does not occur. The possibility that the oxygen scrambling may be a concerted reaction and not involve an ion-pair intermediate is discussed.
View MoreSuzhou Credit International Trading Co., Ltd
Contact:+86-512-65398039
Address:Qingdeng, Hightech. District, Suzhou
Shenyang Xinyihan Chemical Technology Co., Ltd.
Contact:+86-18525026267
Address:362, aigongbeijei street 23 , tiexi district,Shenyang, Liaoning, China
Jewim Pharmaceutical (Shandong) Co., Ltd
Contact:+8615621883869
Address:山东省泰安市高新技术产业开发区配天门大街西首
Contact:+86-27-67841589
Address:Add: 999 Gaoxin Road, Donghu New Technology Development Zone, Wuhan City, Hubei, China
Contact:86-536-8866010
Address:NO.4455 EAST FUSHOU ST. WEIFANG DEVELOPMENT ZONE, SHANDONG, CHINA
Doi:10.1021/jp312241h
(2013)Doi:10.2533/chimia.2007.143
(2007)Doi:10.1246/cl.1984.1747
(1984)Doi:10.1039/P19720000892
(1972)Doi:10.1002/adsc.201300819
(2013)Doi:10.1002/oms.1210090506
(1974)