Dipolar addition reactions of nitrileoxides VI. Reaction of benzonitriloxides with diazomethane

✍ Scribed by K. Nagarajan; P. Rajagopalan

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 248 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70134-1

✦ Synopsis

In the wake of a recent communlcationl In thlr journal, we would like to publieh our obeervatlone on the couree of the reaction between beneonltrlleoxldes and dlaeomethane. Treatment of an ethereal solution of beneonltrlleoxlde with an ethereal eolutlon of dlaeomethane afforded In 25% yield a light yellow crystalline solid, m.p. 151-152' (dec.) of the molecular formula C#i30 (analyele, meee spectrum). This product wae obviouely not canpound II that we hoped to obtain by methylene addition to the nltrlleoxide. Reductive acetylation of the product in dioxane containing acetic anhydride ln the preeence of 10s W-C yielded, after the slow Uptake of 1 mole of hydrogen, a colourleee crystalline compound, C12H12R20, m.p. 132-134* . (,Xmax 286 m,u , 623,000) which wae ldentlfled ae N-acetyl-F phenyl-A2-pyrasollne2. LIAlH4 reduction of the dlaeomethaue product afforded an 011, which wae eventually characterlsed ae l Contribution No.74 from the CIBA Reeearoh Centre, Bombay 63. For Part V of thie eerlee g. P. Rajagopalan and C.N. Talaty Tetrahedron Letters, in preee.