SYNTHESIS OF A NOVEL EXCEEDINGLY STRONG NONIONIC SUPERBASE

Abstract

The synthesis of a novel superbase P(HNCH₂CH₂)(i-PrNCH₂CH₂)₂N, 2a, is discussed. The conditions for the preparation and purification of H₂NCH₂CH₂N(CH₂CH₂N-i-Pr)₂, 4a, starting from commercially available (H₂NCH₂CH₂)₃N (tren) were optimized. The existence of the novel zwitterion HP(N⁻CH₂CH₂)(i-PrNCH₂CH₂)₂N⁺, 2b, was substantiated by NMR spectroscopy. The superbase 2a crystallizes from its melt when cooled slowly to -4 °C, and then remains as a solid at room temperature for several days. Hence it can be handled as a liquid or as a solid.

Key Words:

• Nonionic base
• strong base.
• synthesis
• zwitterion