Further chemical reactions of 1-pyrroline fatty ester: N-substituted pyrrolinium and pyrrolidine derivatives

✍ Scribed by M.S.F. Lie Ken Jie; M.S.K. Syed Rahmatullah

• Book ID: 103037794
• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 589 KB
• Volume: 77
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(95)02465-u

✦ Synopsis

The reactive C=N bond of the l-pyrroline fatty acid ester, methyl 8-(5-hexyl-2-pyrroline-l-yl)octanoate synthesized from methyl is'o-ricinoleate (methyl 9-hydroxy-12-cis-octadecenoate) readily undergoes N-protonation, N-bromination, N-iodination N-nitration, N-nitrosation and N-oxymercuration to give the N-substituted 1-pyrrolinium derivatives by electrophilic addition reactions. Sodium borohydride reduction of the pyrrolinium derivatives yields the corresponding cis and trans N-substituted pyrrolidines. Addition of a nucleophile (CN ) to C=N ' bond of an N-methyl l-pyrrolinium derivative forms trans-2,5,5-trisubstituted N-methyl ester derivative exclusively. The structures of these derivatives were characterized by infrared, ~H and ~3C nuclear magnetic resonance spectroscopy.