Journal of the American Chemical Society p. 1427 - 1431 (1984)
Update date:2022-09-26
Topics:
Nordlander, J. Eric
Kotian, Kirtivan D.
Raff, Dwight E.
Njoroge, F. George
Winemiller, Jeffry J.
The regiochemistry and stereochemistry of addition of CF3CO2D to cyclooctene have been established by 2H NMR analysis of the cyclooctanol derived from the trifluoroacetate product.A complex mixture dominated by (Z)-cyclootanol-2-d (4-OH) and (Z)-cyclooctanol-4-d (8-OH) was obtained after 99percent reaction of the olefin essentially under kinetic control.Determination of the product composition as a function of time and extrapolation to zero, however, established that the trifluoroacetates of 4-OH and 8-OH are the exclusive primary adducts.These and complementary results indicate that the reaction proceeds entirely by stereospecific formation of a 1,5-hydride-bridged carbonium ion which is partitioned between nucleophilic solvent attack and, to a lesser extent, reversion to olefin by nearly completely anti vicinal deprotonation or dedeuterionation.
View MoreContact:86 21 3772 9386
Address:Rm.1803,Starry Bldg.1,1505 Meijiabang Road,Shanghai 201620 China
Shanghai Yongyi Biotechnology Co., Ltd
Contact:+86-0512-69561955
Address:Suite 3005, City Gateway, No.398 North CaoXi Road, XuHui District, Shanghai 200030, China.
Shandong Zhongcheng Barium Salt Co., Ltd
Contact:+86-15725732638
Address:No.29 baoxi road, hi-tech zone, zibo, shandong
TIANJIN BAOLIRUITE CHEMICALS CO.,LTD
Contact:+86-022-58652605
Address:NO.60,xiqing high-end metal products industrial zone, Tianjin, China.
Weihao Chemtech (ChangZhou) Co., Ltd.
Contact:051989185693
Address:NO 217 huangshan Rd ,Changzhou
Doi:10.1016/j.steroids.2017.10.003
(2017)Doi:10.1002/ardp.19763090105
(1976)Doi:10.1016/j.molstruc.2018.07.036
(2018)Doi:10.1021/jo01063a026
(1961)Doi:10.1016/0040-4020(75)80155-4
(1975)Doi:10.1016/S0960-894X(03)00253-1
(2003)