T. Koyano, O. Watanabe
May 1, 1971
Citations
0
Influential Citations
6
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Chlorination of 1-octene with cupric chloride has been investigated in methanol at 110–130°C. The yield of 1,2-dichlorooctane (I) increased by addition of lithium chloride in the reaction mixture, while that of 1-chloro-2-methoxyoctane (II) decreased. Addition of water and cuprous chloride markedly retarded the reaction. The initial rates of formation of I and II could be expressed as v=k[octene]0 [CuCl2]01.6 and v=k[octene]0 [CuCl2]0, respectively. These results can be explained as an initial formation of a complex between olefin and cupric chloride molecule, followed by competitive attack on the complex by chloride ion and methanol. In the less polar reaction media containing more octene, the ratio of I/II increased. This may be ascribed to the steric effect of cupric chloride in the intermediate.