19064-72-3Relevant articles and documents
Electrochemical reduction of 1,4-disubstituted phthalazines
Yanilkin,Buzykin,Morozov,Nastapova,Maksimyuk,Eliseenkova
, p. 1636 - 1646 (2001)
Electrochemical reduction in dimethylformamide of unsymmetrical 1-Cl-4-X-phthalazines and symmetrical 1,4-X2-phthalazines (X = Cl, PhO, MeO, EtO, i-PrO) was studied by voltammetry and electrolysis-ESR. The electron trasfer on 1,4-dichlorophthalazine and unsymmetrical 1-Cl-4-X-phthalazines induces anionoid elimination of Cl and X, pyridazine ring cleavage, and phthalonitrile formation. In this previously unknown process the transfer of two electrons induces cleavage of three σ bonds and formation of two new π bonds. The reduction of 1,4-dialkoxy(diaryloxy)phthalazines involves formation of stable radical anions which undergo no heteroring cleavage. Possible mechanisms of the processes studied were discussed. It was assumed that the same mechanism with pyridazine ring cleavage may be realized with other phthalazine derivatives and heteroannelated pyridazines containing readily leaving nucleofuge groups α to nitrogens.
