Journal of Organic Chemistry p. 876 - 879 (1983)
Update date:2022-08-11
Topics:
Croft, Alan P.
Bartsch, Richard A.
Syn eliminations from trans-1-bromo-2-chlorocyclohexane (1) induced by complex-base combinations of NaNH2-NaOR(Ar) in tetrahydrofuran at room temperature favor dehydrochlorination (54-65percent) over dehydrobromination.Under the heterogeneous reaction conditions, oxyanion bases derived from tertiary, secondary, and branched primary alcohols as well as phenols and 2-butanone are effective complex-base components, which suggests that NaNH2 is the effective base species.Reactions of 1 with NaNH2-Na-t-Bu are not influenced by ultrasonic irradiation, but the propensity for lossof the normally poorer leaving group disappears in the presence of 15-crown-5.Transition states for complex-base-promoted syn eliminations are discussed.
View More
Shanghai Sunwise Chemical Co., Ltd
website:http://www.sunwisechem.com
Contact:86-021-33883180
Address:Room 10E, Building G, Westlink Center, No. 2337 Gudai Road, Minhang District, Shanghai, China PC: 201100
Tianjin Realet Chemical Technology Co.,Ltd.
website:http://www.realetchem.com
Contact:+86-022-58788819
Address:shuanggang industrial park
Contact:+86-512-69561895
Address:No.111, Building A4, 218 Xinghu Street, Suzhou Industrial Park, P. R. China
AstaTech ( Chengdu) BioPharmaceutical Corp.
website:http://www.astabiochem.cn/
Contact:+86-15198215156-15198215156
Address:SICHUAN CHENGDU
Shanghai Witshoot Internet Technology Co Ltd
Contact:+86-21-66390020
Address:Room 419, No.285 Luochuan Road (E)
Doi:10.1039/c0dt00976h
(2010)Doi:10.1016/j.jssc.2009.10.021
(2010)Doi:10.1016/j.poly.2018.11.009
(2019)Doi:10.1021/ja01309a043
(1935)Doi:10.1016/j.tetasy.2011.09.003
(2011)Doi:10.1016/j.tetlet.2019.151471
(2020)
