The Conversion of Isoprene-Carbon Tetrachloride Adducts in Alkali Medium

Abstract

The reaction of isoprene-CCl4 adducts (a mixture of 1, 1, 1, 5-tetrachloro-3-methyl-3-pentene(1) and 1, 1, 1, 5-tetrachloro-4-methyl-3-pentene(2)) with alkali was studied. This reaction proceeds step-wise and the reactivity of the adduct depends on the position of the methyl group towards the trichleromethyl group. 1-Carbomethoxy 4 methoxy-2-methyl-1-butene(9) and 1-carbomethoxy-4-methoxy. 2-methyl-1-butene(10) were obtained from (1), while 1, 1-dichloro-5-methoxy-4 methyl-1, 3-pentadiene(6) was obtained from (2). Furthermore, the model compounds such as 1, 1, 1, 5-tetrachloro-3-pentene(11) and 1, 1, 1, 5-tetrachloro-3, 4-dimethyl3-pentene(12) were synthesized and the reations were tested.
It is concluded that when the methyl group of the adduct is located at β-position towards the trichloromethyl group, the diene is converted to the chloroacetylenic compounds.