K. Uneyama, N. Hasegawa, Hiroyuki Kawafuchi
Apr 1, 1983
Citations
0
Influential Citations
7
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
3-Chloro-2-chloromethyl-4-(4-chlorophenoxy)-1-butene (1) was prepared in 72% yield by electrooxidative double ene-type chlorination of 1-(4-chlorophenoxy)-3-methyl-2-butene. The electrolysis was conducted at room temperature in a two layer solvent system of dichloromethane and water in the presence of acids (HCl, H2SO4, H3PO4, etc). Either 3-chloro-2-methyl-4-(4-chlorophenoxy)-1-butene or 1 was selectively prepared, respectively after 4 or 10 F/mol of electricity were passed using platinum foils as electrodes in an undivided cell. The similar electrolysis of the related 3-methyl-2-butenyl derivatives 2b and 2c provided the ene-type products, 3-chloro-2-methyl-4-benzyloxy-1-butene and 4-chloro-1-ethynyl-1,5-dimethyl-5-hexenyl acetate, respectively. In contrast, 3-methyl-2-butenyl derivatives 2d–f and 3-methyl-2-butenoic acid afforded a variety of products such as chlorohydrin, vinyl chloride, and sulfoxide other than ene-type products, suggesting that the functional group of R in 2 affects the reaction cou...