A novel von richter reaction

✍ Scribed by G.T. Rogers; T.L.V. Ulbricht

• Book ID: 104249501
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 159 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)98882-3

✦ Synopsis

The reaction of p-chloronitrobenzene (I) with potassium cyanide in aqueous alcohol to give m-chlorobenzoic acid as the major product was discovered by van Fichter,l and stulies by Bunnett? snd othw?

have elucidat:?d its mechmism.

We now report that when dimethyl sulfoxide (DXSO) is used as solvent, the reaction takes a complrtely different covse, and s novel series of products is formed.

The reaction of I with excess cyanide in DES0 is complete in two hours at 100' (compared with 48 hours for the reaction in refluvinp aqueous alcohol 2 ) and rives n complex mixture from which we have isolated five crystalline products in P combined yield of 4&.