Rearrangement of Electronegatively Substituted Guanidines to Semicarbazones

✍ Scribed by Doz. Dr. A. Heesing; Dipl.-Chem. H. Schulze

• Book ID: 101550112
• Publisher: John Wiley and Sons
• Year: 1967
• Tongue: English
• Weight: 111 KB
• Volume: 6
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196707041

✦ Synopsis

The silyl derivative of ethyleneimine (4) is obtained pure only wjth difficulty. So it is interesting that use of the products (3) make it possible to transfer the sulfur chain to ( 4 ) .

' (4). Yield ( %)

3. 41

The ring bonds in compound (5) can conjugate with the sulfur chain, as is shown by the bathochromic shift of the absorption maxima of (5) in comparison with those of dipiperidinosulfanes [31. Attempts to distil compound (S) often led to violent explosions.

Di(aziridin-I-yl)sulj&es (5) :

Diimidazol-1-ylsuIfane (3) (0.02 mole) was suspended in anhydrous n-pentane (50 ml) and treated with (4) (0.04 mole) at 5 to 10°C. After storage at -20°C for 5 h the crystalline imidazole was filtered off and the solvent was removed from the filtrate by distillation in a vacuum. The pure compound (5) remained as residue.