Journal of Organic Chemistry p. 3584 - 3587 (1986)
Update date:2022-07-30
Topics:
Fossey, Jacques
Lefort, Daniel
Sorba, Janine
The free radical 6,6-dimethylbicyclo<3.1.1>hept-2-yl (7) has been obtained by decarboxylation of cis- or trans-6,6-dimethylbicyclo<3.1.1>heptane-2-peroxycarboxylic acids (6a and 6b). 7 trapped by reaction with the initial peracid gave a stereochemical mixture of α- and β-nopinol (8a and 8b).The ratio 8b/8a is around 12, independent of the initial peracid 6a or 6b and its initial concentrations.This value is mainly due to the steric effect of one of the methyl groups branched on C7 in 7.The structure of 7 is discussed.By a competitive reaction 7 undergoes ring opening to afford 2-(3-cyclohexenyl)-2-propyl free radical (9) which by reaction upon peracid leads to 2-(3-cyclohexenyl)-2-propanol (10). 7 was successfully trapped because its reaction with peracid is rapid enough.The ratio of the two alcohols 8/10 leads to an estimation of 1*106 M-1 s-1 for the rate constant of the reaction of 7 with peracids
View MoreLianyungang Ningkang Chemical Co., Ltd
Contact:.+86-518-88588008
Address:http://www.chemnk.com
Tangshan Wisdom Trading Co.,Ltd
Contact:86 315 2222979
Address:No.41 BeiXinXi Road, Yangguang building 1-1102 , Tangshan, Hebei, China
Tai zhou world Pharm & Chem Co., Ltd
Contact:+86-576-85301198
Address:Rome 1001,wangjiang plaza,unti 2,jinshan east Road linhai,zhejiang,china
Chengdu Chengnuo New-Tech Co., Ltd
Contact:0086-028-85749078
Address:4 Jiuyang road,Jiulong industrial port,Chengdu, China
TIANJIN BAOLIRUITE CHEMICALS CO.,LTD
Contact:+86-022-58652605
Address:NO.60,xiqing high-end metal products industrial zone, Tianjin, China.
Doi:10.1021/acs.oprd.8b00318
(2018)Doi:10.1002/hlca.19570400611
(1957)Doi:10.1002/chem.200305588
(2004)Doi:10.1016/0040-4020(95)00595-Y
(1995)Doi:10.1016/j.tetlet.2010.03.043
(2010)Doi:10.1016/j.poly.2012.10.013
(2013)