Pyrolysis of aminonitriles, cyanohydrazones, and cyanoacetamides. Part I. Elimination reaction of 1-arylmethyleneamino-1,2-dihydro-4,6-dimethyl-2-oxopyridine-3-carbonitriles and substituted benzaldehyde cyanoacetylhydrazones
✍ Scribed by Nouria A. Al-Awadi; Mohamed H. Elnagdi; Tommy Mathew; Ibrahim El-Gamry; Mervat Abdel Khalik
- Book ID
- 101256475
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- English
- Weight
- 330 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0538-8066
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✦ Synopsis
Pyrolysis of the Schiff bases of 1 -arylmethylenearnino-l.2-dihydro-4.6-dirnethyl-2-oxopyr1dine-3-carbonitriles [ 1-5) has been studied These compounds eliminate via a six-membered transition state to produce substituted benzonitriles and 2-hydroxy-4.6-dirnethylpyridine-3- carbonitrile. These eliminations are unimolecular first-order reactions. The kinetic data gave a good correlation with (TO values of the substituents on the aryl group with p = 0 83 at 520 K. Utilization of the pyrolytic reaction in synthesis of various benzonitriles is considered, and mechanistic information has been obtained by comparing the kinetic data and product analysis of the Schiff bases with their open-chain substituted benzaldehyde cyanoacetylhydrazones (6-9) analogues 0 1996 J o h n Wiley & Sons, Inc