Direct Synthesis of N-Arylquinone Imine Acetals and Quinol Imines from Acetals

✍ Scribed by M. Carmen Carreño; Juan M. Cuerva; María Ribagorda; Antonio M. Echavarren

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 115 KB
• Volume: 38
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/(sici)1521-3773(19990517)38:10<1449::aid-anie1449>3.0.co;2-m

✦ Synopsis

In the absence of any added acidic catalyst quinone acetals as well as simple ketone and aldehyde acetals react with a variety of substituted anilines to form imines [Eq. (a)]. Contrary to what is expected from arguments based on their nucleophilicity, the most reactive anilines are those bearing electron-withdrawing groups.