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Original Articles

Synthesis and Structure of Aminophosphonates Containing 3,5-Di-Tert-Butyl-4-Hydroxyphenyl and Acetal Groups

, , , , , , & show all
Pages 2283-2290 | Received 28 May 2015, Accepted 07 Jul 2015, Published online: 10 Dec 2015
 

GRAPHICAL ABSTRACT

Abstract

The reactions of dialkyl [(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadienyl)methyl]phosphonates with N-nucleophiles (aminoacetaldehyde dimethyl acetal and diethyl [(2,2-dimethoxyethyl)aminomethyl]phosphonate give new aminophosphonates containing the 3,5-di-tert-butyl-4-hydroxyphenyl substituent, in addition to the acetal group. The crystal structure of diethyl {(3,5-di-tert-butyl-4-hydroxyphenyl)[(2,2-dimethoxyethyl)amino]methyl}phosphonate is elucidated. The presence of a chiral carbon atom and prochiral phosphorus atom in the aminophosphonate products is responsible for the complicated pattern in the 1H NMR spectra, the features of which are discussed.

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