ChemInform Abstract: Synthesis and Reaction of Cyanonitrochloro(ethoxycarbonyl)methane with Benzonitrile N-Oxide and Its Derivatives.

✍ Scribed by A. G. Tyrkov; E. V. Shevchenko; G. G. Lavrenenko

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 28 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199946143

✦ Synopsis

Synthesis and Reaction of Cyanonitrochloro(ethoxycarbonyl)methane with Benzonitrile N-Oxide and Its Derivatives.

-Reaction of the title ethoxycarbonylmethane (II), prepared from the potassium salt of cyanonitro(ethoxycarbonyl)methane and HCl, with benzonitrile oxide (I) proceeds by 1,3-dipolar addition to afford phenyloxadiazole derivative (III). In contrast, in the reaction with nitrobenzonitrile oxides (IV) the dipolarophilic activity of the cyano group of compound (II) is not high enough to initiate a dipolar addition, thus, only dimerization of the nitrile oxide to furoxanes (V) is observed. -(TYRKOV, A.