The diverse behaviour of the P-Cl bonds in the spiro-cis-ansa spermidine derivative cyclotriphosphazene towards mono-functional nucleophilic reagents

Abstract

A number of new spiro-ansa spermidine derivative cyclotriphosphazenes (2-10) is synthesized in order to provide insight into the reaction mechanism for nucleophilic substitution. The structures of the compounds were determined by elemental analysis, mass (MS), H-1, F-19 (for 9) and P-31 NMR spectroscopies. Compounds (2-8) and 9, 10 can be formed by a proton abstraction-chloride elimination and both the S-N(1) and S-N(2) reaction mechanisms, respectively. (C) 2009 Elsevier B.V. All rights reserved.