Chemistry of Heterocyclic Compounds p. 268 - 272 (1985)
Update date:2022-08-11
Topics:
Bespalov, B. P.
In the reaction of tricynoethylene (TCE) with phenoxazine in DMF at 100 deg C, in addition to the principal reaction product - viz., 3-(tricynovinyl)phenoxazine - 3-dicyanomethylene-3H-phenoxazine and 3-phenoxazinyl-3-(3H-phenoxazinylene)-cyanomethane are formed in small amounts.The latter two compounds were also obtained from phenoxazine and dibromomalononitrile.Phenothiazine reacts similarly with tetracyanoethylene.A reaction scheme is proposed, and in this scheme the formation of side products is explained by significant electron transfer in the tetracyanoethylene-heterocycle system.For the first time, 1,6 cleavage of HCN was detected, in which (in contrast to the known 1,6 cleavage of HCN from carbon atoms) the hydrogen is split out from the nitrogen atom.
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