Chemical and Pharmaceutical Bulletin p. 296 - 306 (1996)
Update date:2022-08-05
Topics:
Ohwada, Tomohiko
Uchiyama, Masanobu
Tsuji, Motonori
Okamoto, Iwao
Shudo, Koichi
We characterized experimentally the substituent effect of a 5-exo substituent on the π facial selectivities of bicyclo[2.2.2]octenes toward electrophilic oxidative reactions such as epoxidation and dihydroxylation, and we discuss the underlying orbital interactions of vicinal σ orbitals and the olefinic π orbital involved in bicyclo[2.2.2]octenes, and commonly in methylenenorbornanes. Of significance is the out-of-phase motif of these σ- π couplings. Electron-withdrawing substituents such as cyano and carboxylic acid groups unequalize the relevant σ-π coupling, leading to the observed syn-facial preference. Alkyl substituents exhibit an electron-donative perturbing effect, depending on the bicyclic ring system.
View Morewebsite:https://sdjingyuan.lookchem.com/
Contact:86-531-82687998
Address:Factory Building 11, Jinan Comprehensive free trade zone, Shandong, China
website:http://www.hope-chem.com
Contact:86-21-58090396-805
Address:Floor 4, Building 5, No.588 Tianxiong Road, Zhoupu International Medical Zone, ShangHai, China
guide(suzhou) fine materials co. ltd
Contact:0512-80972173
Address:21st Building, No.369 Lushan Rd, New District Suzhou China 215129
Taixing Shenfeng Chemical Co., Ltd.
Contact:+86-523-87117033, 87117666
Address:4# Yinsanlu, Huangqiao town, Taixing, Jiangsu, China.
Sichuan Mianzhu Ronghong Chemical Co.,LTd
Contact:8613981840544
Address:XINSHI INDUSTRY PARK,MIANZHU,SICHUAN,CHINA
Doi:10.1039/b104523g
(2001)Doi:10.1039/jr9560001521
(1956)Doi:10.1021/jo00389a051
(1987)Doi:10.1039/jr9380001578
(1938)Doi:10.1016/S0040-4039(01)01824-X
(2001)Doi:10.1016/0022-328X(88)80553-9
(1988)
