Nitroalkanes as Alkyl Anion Synthons — A New Approach to the Synthesis of 2-SubstitutedN-Ethyl Succinimides and 2-Substituted Succinate Diesters via Nitroalkanes

✍ Scribed by Ballini, Roberto ;Bosica, Giovanna

• Book ID: 102365932
• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 256 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619961221

✦ Synopsis

Abstract

2‐Substituted N‐ethyl succinimide and 2‐substituted succinate diesters were obtained by two key steps: (i) Michael addition of a nitroalkane to the appropriate enedione derivative under basic conditions (DBU), with the concomitant elimination of nitrous acid, and (ii) selective reduction of the obtained enone with nickel boride, in methanol/THF. In this context the nirtoalkane acts as an alkyl anion synthon. By this method trimethyl tricarboxylates were also synthesized.