Intermediates in the Reactions of Chloranil and 2,6-Dichloro-1,4-benzoquinone with Pyrrolidine

Although the intermediates in the reactions of chloranil and 2,6-dichloro-1,4-benzoquinone with pyrrolidine are the corresponding monoaminated chloroquinones, these compounds exhibit a pronounced tendency to form molecular complexes; thus, the spectral characteristics of 2,3,5-trichloro-6-pyrrolidino-1,4-benzoquinone indicate its partial self-complexation into the corresponding biradical dimer. 2,6-Dichloro-3-pyrrolidino-1,4-benzoquinone forms a stable quinhydrone complex with 2,6-dichlorohydroquinone.