Synthesis and properties of dipyridinium betaines of derivatives of 1,4-benzoquinone and tetracyanoquinodimethane

Abstract

Reaction of chloranil with excess pyridine gives the poorly stable 2,5-di(N-pyridinium)-3,6-dichloro-1,4-benzoquinone dichloride which is readily hydrolyzed to give the bisbetaine of 2,5-di(N-pyridinium)-1,4-benzoquinone-3,6-dioxide. Treatment with acid gives its mono- and bisprotonated derivatives as the perchlorate and dibromide and bromination gives the betaine 2-bromo-2,5-di(N-pyridinium)-5-cyclohexene-1,3,4-trione-6-oxide perbromide. The reaction of malonodinitrile with 2,5-di(N-pyridinium)-3,6-dichloro-1,4-benzoquinone dichloride in situ gives the poorly stable bisbetaine of 2,5-di(N-pyridinium)-7,7,8,8-tetracyanoquinodimethane-3,6-dioxide.

How to Cite
Yanchishin, V. A.; Karlivan, G. A.; Valter, R. É. Chem. Heterocycl. Compd. 1998, 34, 312. [Khim. Geterotsikl. Soedin. 1998, 34, 346.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02290722