The System Potassium Amide/Ammonia

✍ Scribed by Prof. Dr. P. W. Schenk; cand. chem. H. Tulhoff

• Publisher: John Wiley and Sons
• Year: 1962
• Tongue: English
• Weight: 238 KB
• Volume: 1
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196206613

✦ Synopsis

The infrared spectrum shows two typical NH2 vibrational bands at 3495 and 3380 cni I and a C-C vibrational band at 1641 cm-1, which are not i l l the spectrum OF the starting material, and the C s N band at 2186 cm.-I is about 50 cm-1 lower than that in the starting material owing to conjugation of the C E N group with the C-C group. The substance evolves 1.04 mole Nz with HN02, in agreement with formula ( 2 ) , which contains a primary amino group. Adipodinitrile gave 2-amino-I-cyanocyclopent-I-ene by the method of 7 I i o n i p ~v n [ I ] using sodium t-butoxide as condensing agent. In the same manner. ( 2 ) can also be obtained from piperidinoacetonitrile. This conlirms that ( 2 ) contains the same enaminonitrile grouping N C C C NH2 as does 2-amino-I-cyanocyclopent-I-ene ( 3 ) .