Journal of the Chemical Society. Perkin transactions II p. 1327 - 1330 (1986)
Update date:2022-08-03
Topics:
Geribaldi, Serge
Decouzon, Michele
Boyer, Bernard
Moreau, Claude
The rate constants for addition of sodium borohydride to 3-substituted 5,5-dimethylcyclohex-2-enones (1), para-substituted 3-phenylcyclohexenones (2), and para-substituted acetophenones (3) have been determined in an alkaline solution (NaOH, 0.025 mol l-1) of water-dioxane (1:1 v/v) at 298 K.The conjugated cyclohexenone systems (1) and (2) undergo exclusive 1,2-reduction in these conditions to produce the corresponding allylic alcohols.The regioselectivity of reduction is discussed.The linear free energy relationships obtained between the rate constants and ?p or ?p+ confirm that these 3-substituted cyclohexenone structures are good models for the investigation of the substituent effects on the reactivity of ethylenic systems.Comparison of reaction constants for the three series leads to the conclusion that, as for borohydride reductions of acetophenone, the cyclohexenone reduction must have a late transition state in the final quarter of the reaction co-ordinate.
View MoreContact:86-571-86737118-8689
Address:No.69, 12 Street, HEDA, Hangzhou, Zhejiang, China
Zhejiang Haizhou Pharmaceutical Co., Ltd.
website:https://www.haizhoupharma.com/
Contact:+86-576-88221016
Address:No. 19, Donghai 5th Avenue, Yanhai Industrial Zone, Linhai, Zhejiang, China
hangzhou sunchem trading co., ltd.
Contact:13588470430--
Address:Room 406-407, the 4th Building, No549
website:http://www.weichichem.com
Contact:+8613912949432
Address:Fine Chemical Industrial Base,Wujiang town,He County,Anhui China.
Shanghai Kefu Chemical Co.,Ltd.
Contact:+86-21-34616196
Address:Room601-602, Xuhui Business Building, No.168, Yude Road, Shanghai
Doi:10.1021/jo001397s
(2001)Doi:10.1016/S0020-1693(00)00202-4
(2000)Doi:10.1016/0040-4039(80)88017-8
(1980)Doi:10.1021/jacs.9b12043
(2020)Doi:10.1021/jo00315a020
(1981)Doi:10.1016/0040-4020(80)85061-7
(1980)
