Chlorinations of tetramethylallene (3), 1, l-dimethylallene (8), and allene have been carried out in nonpolar media in the presence of oxgen as a radical inhibitor. The only chlorination product of 3 at 25" in C2FsC18 solution is 3-chloro-2, 4-dimethyl-l, 3-pentadiene (4). However, the hydrogen chloride coproduct leads to extensive isomerization of 3 to form 2, 4- dimethyl-l13-pentadiene(5) and subsequent telomerization of 5 in large part to 1, 3, 3, 5, E ...
