Journal of the Chemical Society. Perkin transactions II p. 175 - 184 (1981)
Update date:2022-08-16
Topics:
Craze, Gabrielle-Anne
Watt, Ian
The hydroxyketones (1) and (2) have been prepared from the Diels-Alder adducts of p-benzoquinone with cyclopentadiene and cyclohexa-1,3-diene.The boron trifluoride-ether catalysed reaction of cyclohepta-1,3-diene with p-benzoquinone gave good yields of the Diels-Alder adduct which was converted into hydroxyketone (3).Experiments with cyclohexanol and admantan-2-ol established characteristic 13C n.m.r. chemical shifts associated with deprotonation of alcohols by dimsyl sodium in dimethyl sulphoxide.Solutions of the sodium salts of (1)-(3) were prepared and dynamic 13C n.m.r. spectroscopy gave barriers for their degenerate rearrangement of >21.7 (100 deg C), 19.0 (100 deg C), and 17.3 (72 deg C) kcal mol-1, respectively.The relationship between variation of barrier and molecular geometry is discussed with the aid of empirical force field calculations.
View MoreContact:0512-63006287
Address:no.88.YISHENG Road,etdz-WUJIANG,SUZHOU,CHINA
Contact:86-379-63338609
Address:Jiudian Village,Deting Town,Song County,Luoyang
WUXI KINGHAN BIO-MEDICAL&CHEMICAL INC.
Contact:13861062998
Address:Room 1316,No.1619 Huishan Avenue,Wuxi,China
Contact:+86-571-87859231, 87859237, 87859239
Address:1606,Huarong Times Mansion, No.3880 Jiangnan Avenue, Binjiang District, Hangzhou, China, 310053
website:http://www.vanzpharm.com/en/index.html
Contact:86-27-84492310
Address:FANHU INDUSTRY PARK
Doi:10.1149/1.2113970
(1985)Doi:10.1002/ardp.19743070602
(1974)Doi:10.1246/cl.2007.1060
(2007)Doi:10.1002/ejic.201801096
(2019)Doi:10.1021/acs.joc.9b00430
(2019)Doi:10.1039/C8NJ03776K
(2019)
