Abstract
In the reaction of tricyanoethylene (TCE) with phenoxazine in DMF at 100 ° C, in addition to the principal reaction product —viz., 3-(tricyanovinyl) 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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
B. P. Bespalov and E. V. Getmanova, Khim. Geterotsikl. Soedin., No. 3, 317 (1981).
P. G. Farrel and R. K. Wijtowski, J. Chem. Soc., C, 1390 (1970).
V. I. Ivanskii, The Chemistry of Heterocyclic Compounds [in Russian], Vyssh. Shkola, Moscow (1969), p. 387.
K. Dietz, H. J. Keller, D. Höhe, and D. Wehe, J. Am. Chem. Soc., 104. 7581 (1982).
Organic Syntheses [Russian translation], Collective Vol. 11, Inostran. Lit. (1961), p. 54.
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 326–330, March, 1985.
Rights and permissions
About this article
Cite this article
Bespalov, B.P. Tricyanovinylation of phenoxazine and phenothiazine. Chem Heterocycl Compd 21, 268–272 (1985). https://doi.org/10.1007/BF00506662
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00506662