Triselenium Dicyanide from Malononitrile and Selenium Dioxide: One‐Pot Synthesis of Selenocyanates.

Abstract

Organo-selenium compoundsOrgano-selenium compounds S 0130 Triselenium Dicyanide from Malononitrile and Selenium Dioxide: One-Pot Synthesis of Selenocyanates. -Malononitrile reacts with selenium dioxide in DMSO to give triselenium dicyanide (II). Addition of aromatic amines, indoles and active methylene compounds produces the corresponding selenocyanates in one pot. -(KACHANOV*, A. V.; SLABKO, O. Y.; BARANOVA, O. V.; SHILOVA, E. V.; KAMINSKII, V. A.; Tetrahedron Lett. 45 (2004) 23, 4461-4463; Dep. Chem., Far East. State Univ., Vladivostok 690950, Russia; Eng.) -Mais 37-173

Thio- and Selenocyanation Reactions of Quinone Imines—Derivatives of Pyrido[1,2-a]benzimidazole

“…[13] Similarly, quinone imines 1a-e react with triselenodicyanide at ambient temperature in one pot selenocyanation reaction in a quinoid kernel. [9] Reaction is accompanied by selective formation of 9-selenocyanoquinone imines 3a-e of the specified series. The reaction is supposed to have an electrophilic character because the selenocyanation of arylamines is accelerated by the electron-donating substituents.…”

“…Compounds 1a-e, dithiocyanogen and triselenodicyanide, were prepared by reported procedures. [14,15,9] Thiocyanates 2a-d: Typical Experimental Procedure…”

“…[8] Recently, we developed a new, simple, and convenient method of one pot selenocyanation of aromatic amines, indoles, and methyleneactive compounds with the help of triselenodicyanide, obtained by oxidative coupling of malononitrile and SeO 2 . [9] Earlier, triselenodicyanide was used as a selenocyanation reagent (in reaction with aniline and N,N-dimethylaniline [10] and also polystyrene [11] ) and cyanation reagent (in synthesis of cyano N-heterocycles [12] ).…”

Synthesis and Antibacterial Activity of Some New Azo Disperse Dyes Containing Selenium and their Application in Polyester Printing

“…The color strength (K/S value) was assessed using Kubelka-Munk equation. (1) [12] To a well stirred solution of malononitrile (0. 2 g, 3 mmol) in DMSO (2 mL), SeO 2 (0.67 gm, 6 mmol) was added.…”