Tetrahedron p. 4417 - 4423 (1987)
Update date:2022-08-22
Topics:
Carretero, J.C.
Ruano, J.L. Garcia
Martinez, M.C.
Rodriguez, J.H.
In order to obtain evidence about the ability of the sulphone group as anchimeric assistant, the behaviour of the erythro and threo-1,2-dimethyl (and 1,2-diphenyl)-2-halo-1-methylsulphonylethanes in their reactions with NH4OH/CH3CN, NaOH/MeOH and AgBF4/MeOH is described.The participation is not detected in any case on butane derivates or on 1,2-diphenylethane derivatives with basic nucleophiles, which yielded mainly elimination products.Reactions of the last compounds with AgBF4/MeOH only afforded mixtures of substitution products, with predominance of those with the same configuration of the starting sulphones in the case of erythro-derivatives, which must only evolve through an SN1 mechanism in competition with the anchimeric assistant process.This is the first reported result suggesting that the weak nucleophilic character of the sulphonylic oxygens can determine its participation as anchimeric assistant in the substitution of good leaving groups in β-position.
View MoreZhejiang Rongkai Chemical Technology Co.,Ltd.
Contact:+86-578-8185786
Address:Shangjiang Industrial Zone,Suichang
Sinoway International (Jiangsu) Co., Ltd.
Contact:+86-25-86630167
Address:17 Beijing Road (West), Nanjing, China
Changsha Huajing Powdery Material Technological Co., Ltd.
Contact:86-731-88879686
Address:Building 2, West Garden, Main Campus of Central South University, Changsha, Hunan Province, China
Dongguan Albiya Energy Science and Technology Co.,Ltd
Contact:+86-769-22181286
Address:Huanan Industial Park, Dongguan,China
Hubei Onward Bio-Development Co., Ltd.
Contact:+86-718-8417012
Address:No.517,Shizhou Avenue,Enshi City,Hubei Province,China,445002
Doi:10.1021/ja01855a010
(1941)Doi:10.1016/j.elecom.2020.106784
(2020)Doi:10.1039/c6sc00798h
(2016)Doi:10.1002/cctc.201501056
(2016)Doi:10.1016/S0040-4039(99)02112-7
(2000)Doi:10.1021/j100105a019
(1993)