First Synthesis of N-Methylene-Ynamines (2-Azabut-1-en-3-ynes)

✍ Scribed by Prof. Dr. Ernst-Ulrich Würthwein; Dipl.-Chem. Reinhard Weigmann

• Book ID: 101557667
• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: English
• Weight: 247 KB
• Volume: 26
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198709231

✦ Synopsis

Compound 1 (1.5 g, 7 mmol) was condensed into a 250-mL flask equipped with a PTFE stopcock and containing 4 (0.66 g, 7 mmol). The flask was allowed to stand at room temperature. After 1-2 d, yellow crystals began to collect on the walls of the flask. At intervals of 2-3 d, 7 mmol of I was condensed three times into the flask. After a further 3 d of reaction, the readily volatile components (0.4 g) were distilled off at room temperature into a 100-mL flask equipped with a stopcock. Their vapor-phase IR spectrum showed exclusively the bands corresponding to unreacted 1 and 4. The crystalline residue was dissolved in 100 mL of CHf.3.. After removal of the solvent by rotory evaporation. sublimation was carried out in vacuum mbar) onto a cold finger at -20°C. Yield: 3.6g 7 (95%); yellow crystals, m.p.= 102°C.