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CHEMISTRY OF DIENES AND THEIR DERIVATIVES XV. PRODUCTS FROM LOW-TEMPERATURE CHLORINATION OF 1,1,2-TRICHLORO-3-METHYL-1,3-BUTADIENE
Kaplanyan, E. E.,Mkryan, G. G.,Adamyan, A. P.,Mkryan, G. M.
, p. 1836 - 1838 (2007/10/02)
The low-temperature chlorination of 1,1,2-trichloro-3-methyl-1,3-butadiene in the presence of tert-butylpyrocatechol leads to 1,1,2-trichloro-3-chloromethyl-1,3-butadiene, 1,1,2,4-tetrachloro-3-methyl-1,3-butadiene, and 1,1,2,3,4-pentachloro-3-methyl-1-butene in ratios of 45.2:18:36.8 respectively.Unlike other dienes 1,1,2-trichloro-3-methyl-1,3-butadiene does not form a 1,4-addition product.During chlorination in the absence of tert-butylpyrocatechol the amount of the product from normal addition increases on account of the simultaneous radical chlorination reaction, and a product from further chlorination of 1,1,2-trichloro-3-chloromethyl-1,3-butadiene, i.e., 1,1,2,3,4-pentachloro-3-chloromethyl-1-butene, is formed.
