The interaction of chloranil with aliphatic amines

Abstract Although substitution of chlorine usually occurs in the interaction of chloranil with aliphatic amines, solutions of chloranil in pure triethylamine yield a product which appears to be a salt, the anion of which is the free radical semiquinone ion derived from chloranil. In acetone solution this salt decomposes to yield 2,3,5‐trichloro‐6‐(2′‐diethylaminovinyl)‐p‐benzoquinone.