Structural Features of Primary 6-Aminopentafulvenes and Some of Their Derivatives

✍ Scribed by Doris Kunz; Roland Fröhlich; Gerhard Erker

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 324 KB
• Volume: 2001
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200109)2001:18<3531::aid-ejoc3531>3.0.co;2-9

✦ Synopsis

Starting from 6-amino-6-methylpentafulvene (2) ''ortho''-Cacylation or N-acylation can be achieved selectively. Treatment of 2 with phthaloyl-protected amino acid chlorides derived from alanine (3a) or valine (3b) leads exclusively to the formation of the ''ortho''-C-acylated derivatives 4, isolated as racemates. Optically active N-acylated products 7 were prepared by coupling 5, obtained by NH deprotonation of 2, with the 1-hydroxybenzotriazole (HOBt) active-esters of [