A New Rearrangement of Substituted 3-Aminopropenals

✍ Scribed by Dr. M. Neuenschwander; Prof. Dr. K. Hafner

• Publisher: John Wiley and Sons
• Year: 1968
• Tongue: English
• Weight: 151 KB
• Volume: 7
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196804601

✦ Synopsis

2-en-1-a1 ( l a ) 121, 4-(dimethylamino)but-3-en-2-one (lb) 131, and methyl 3-(dimethylamino)acrylate (Ic) [41 leads almost quantitatively t o the hydrobromides (2). which react with triethylamine t o give the bromine derivatives (3) in yields of more than 90 % [51. The acetylenes (4) are obtained from (3) in yields of about 70 % by elimination of HBr with potassium rert-butoxide [61. Compound (4a), a pale yellow oil, is stable for long periods only below -5OoC, whereas (4b) and (4c) can be kept for several hours at room temperature.