γ-Radiolysis of chloranil in benzene

Abstract

Γ-Radiolysis of chloranil in benzene gave four products: the quinones 3,6-di-chloro-2,5-diphenyl-1,4-benzoquinone (11) and 2-chloro-3,5,6-triphenyl-1,4-benzo-quinone (12), and small amounts of 2,3,5-trichloro-6-phenylhydroquinone (10) and 1,3,4-trichloro-2-hydroxydibenzofuran (14; R = H). The last compound only was formed when radiolysis was carried out in the presence of oxygen. Syntheses of 2,3,5-trichloro-6-phenylhydroquinone (10), 2,3,6-trichloro-6-phenyl-1,4-benzoquinone (9), and 2-chloro-3,5,6-triphenyl-1,4-benzoquinone (12)are described.