Synthesis of diaza [7,7] paracyclophanetetraene and diaza [7,2,7,2] paracyclophanehexaene

✍ Scribed by Patrick Bauchat; André Foucaud

• Book ID: 104244969
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 82 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93887-0

✦ Synopsis

The diazabicyclooctane -catalyzed reaction of terephthalaldehyde with methyl acrylate gave the diester 2 or the monoester 4. The diester 2, acetylated and treated with ammonia gave a diaza 17,7] paracyclophane 6 and the macrobicycle 7. The diester 8, obtained by the titanium induced reductive coupling reaction of the acetylated ester 5, was treated by NH3 to give a diaza paracyclophane.