Tetrahedron p. 2311 - 2318 (1988)
Update date:2022-08-02
Topics:
Jursic, Branko
Ladika, Mladen
Bosner, Branka
Kobetic, Renata
Sunko, Dionis E.
In an attempt to study possible ?-participation in allyl-dervatives, 3-alkenyl-5,5-dimethyl-2-cyclohexenyl p-nitrobenzoates 4 and 2-alkenyl-3-methyl-2-cyclohexenyl p-nitrobenzoates 5 were solvolyzed in 97 wt percent trifluoroethanol and 80 vol percent ethanol.Water soluble 1-methyl-3-(3-alkenyl-5,5-dimethyl-2-cyclohexenyl)pyridinium iodides 6 were solvolyzed in water and in aqueous solvents, as well as under micellar conditions.All esters show in each of the solvents normal values of secondary α-deuterium isotope effects (kH/kD = 1.17-1.23).Also in comparison to saturated analogues the investigated esters show a lower solvolytic reactivity.On the basis of these results it was concluded that the solvolysis proceeds via a stepwise mechanism involving a resonance-stabilized cyclohexenyl cation as the reaction intermediate.
View MoreFujian Huitian Biological Pharmacy Co., Ltd.
Contact:0086-598-8300831; 8339920
Address:No.46,Taijiang Road,Sanming City,Fujian,China
Shandong Loyal Chemical industrial Co.,Ltd
Contact:0533-7451788
Address:Linzi Chemical Industrial Park, Zibo, Shandong Province
Tai zhou world Pharm & Chem Co., Ltd
Contact:+86-576-85301198
Address:Rome 1001,wangjiang plaza,unti 2,jinshan east Road linhai,zhejiang,china
lianyungang jinkang pharmaceutical technology co., ltd.
Contact:008651885445517
Address:Jinshan industrial park, Ganyu county, Lianyungang, Jiangsu Province, 222115, China
Zhejiang Sanmei Chemical Industry Co., Ltd
Contact:86-579-87633213
Address:Huchu Industrial Zone, Qingnian Rd., Wuyi County, Zhejiang Prov., China.
Doi:10.1039/b804260h
(2008)Doi:10.1021/jacs.6b13168
(2017)Doi:10.1002/chem.200900623
(2009)Doi:10.1002/anie.200901962
()Doi:10.1016/0223-5234(88)90013-X
(1988)Doi:10.1021/ol901290z
(2009)