Journal of Organic Chemistry p. 3983 - 3987 (1984)
Update date:2022-08-05
Topics:
Pollack, Ralph M.
Kayser, Robert H.
Cashen, Michael J.
Rates of both acid-catalyzed and base-catalyzed enolization of trans-hexahydrofluorenone (trans-HHF) have been measured and compared with those for a variety of other ketones.It was found that trans-HHF enolizes substantially faster than cyclohexyl phenyl ketone (CPK) in both acid (1800-fold) and base (2650-fold).This rate variation is thought to be due to two factors. (1) In trans-HHF the cleaving C-H bond is held rigidly parallel to the ? orbital of the ketone.About a factor of 25- to 60-fold is attributed to this stereoelectronic effect. (2) There are stericinteractions in the enol of CPK which decrease its rate of enolization by about 40- to 50-fold.
View MoreShanghai Rainbow Chemistry Co., Ltd.
Contact:+86-21-64968086-5815/5812
Address:3rd floor, Building 7, 251 Faladi Road, Zhangjiang Hi-Tech Park, Pudong District, Shanghai, P.R. China
Hebei Lead Bio-Chemicals Co., Ltd.
website:http://www.ldbiochem.com
Contact:+86-311-87826503
Address:481, Heping West Road, Shijiazhuang,China
Nanjing Capatue Chemical Co., Ltd
Contact:+86-25-86371192 +86-025-85720158
Address:No.20 Jiangjun Avenue, Jiangning Economic & Technical Development Zone
Synchem Pharma Co.,Ltd(expird)
Contact:+0086-21-61984905-1
Address:Building 60,Zimian Park, LongYang industrial Area, 1515Nong，Yuandong Road Fengxian District, Shanghai ,China
Lianyungang Ningkang Chemical Co., Ltd
Contact:.+86-518-88588008
Address:http://www.chemnk.com
Doi:10.1039/J39710000103
(1971)Doi:10.1002/jps.2600591039
(1970)Doi:10.1021/jm00283a013
(1971)Doi:10.1007/BF00854249
()Doi:10.1007/BF00943909
()Doi:10.1021/ja01394a020
(1928)
