Tandem addition-rearrangement of nitrile anions to benzyne. A convenient synthesis of 3-cyano-2-alkyl benzoic acids and benzaldehydes.

✍ Scribed by A.I. Meyers; Paul D. Pansegrau

• Book ID: 104233700
• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 186 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81332-0

✦ Synopsis

Benzynes derived from aryloxazolines react with lithio-alkyl nitriles to give addition followed by cyclization to benzocyclobutanone imines which fragment to the title products.

We have described the synthetic utility of benzynes, generated from m-chlorophenyloxazoline 1, to give 1,2,3_trisubstituted benzoic acids (A)'. We now report that this readily accessible benzyne reacts smoothly with lithioalkyl nitriles to produce 3-cyano-2-alkyl benzoic acids or benzaldehydes, after oxazoline removal (B).