The Reaction of Phenyldichlorophosphine with Bis(Salicylidene)Ethanediamine—A New Approach to Aza-Crown Derivatives

GRAPHICAL ABSTRACT

Abstract

Reaction of dichlorophenylphosphine with bis(salicylidene)ethanediamine in the presence of triethylamine is proposed to lead to the formation of spirophosphoranes bearing 1,4-piperazine and tetraaza-12-crown-4 ester moieties. The hydrolysis of the putative spirophosphoranes gives mixtures of [2,3-bis-(2-hydroxyphenyl]-1,4-piperazine, its phenylphosphonic derivative and the mono- and diphenylphosphonic derivatives of 2,3,7,8-tetrakis(2-hydroxyphenyl)tetraaza-12-crown-4 ester, whose structures were supported by mass spectroscopy MALDI and ESI.

Keywords:

• Spirophosphorane
• bis(salicylidene)ethanediamine
• 1,4-piperazine
• tetraaza-12-crown-4 ester
• phenylphosphonic acid ester
• macrocyclization