The cycloaddition reaction of isonitriles (the reaction of isonitrile with diazoalkane)

✍ Scribed by Michihisa Muramatsu; Naruyoshi Obata; Takeo Takizawa

• Book ID: 104238161
• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 211 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)86826-x

✦ Synopsis

Isonitriles react with carbenes to give @-adducts, keteneimines. 1) Further cycloaddition of isonitriles to keteneimines is expected when the substituents of them are aromatic. From this point of view, reaction of several aromatic isonitriles with diazoalkanes as the precursors of carbene was examined. Photolysls of diphenyldiazomethane (I), in the presence of equimolar 2,6dimethylphenyl-(IIa) or phenylisonitrile (IIb) In n-hexane at room temperature, gave keteneimine (IIIa, mp 60-lo(!), acetamide (IVa, mp 210-1°C: IVb, mp 177-8'(Z), a hydrated product of III, and small amounts of violet crystals (Va, mp 197-8°C: