Reaction chemistry of tri-substituted mesitylene derivatives and the synthesis of sterically buttressed 1, 3, 5-triaminocyclohexyl ligands

AS Batsanov, JAK Howard

Index: Parker, David; Senanayake, Kanthi; Vepsailainen, Jouko; Williams, Stefania; Batsanov, Andrei S.; Howard, Judith A. K. Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 8 p. 1445 - 1452

Full Text: HTML

Citation Number: 0

Abstract

The sterically buttressed triamine cis, cis-2, 4, 6-trimethyl-1, 3, 5-triaminocyclohexane is weakly basic in aqueous solution (pKa: 7.83, 6.73, 5.15; 298 K) because of steric inhibition to solvation. As a result of intramolecular hydrogen-bonding and stabilising σC–H–σ* C–N interactions, the free amine and its monoprotonated salt adopt a conformation in which the three amino groups are axially disposed. It possesses a reduced reactivity in SN2 ...