Reactions of 3-methyl-1,2-butadienylphosphonates with 4,9-dioxa-1,12-dodecanediamine

Abstract

High reactivity of allene derivatives of the tetracoordinated phosphorus atom in the nucleophilic addition reactions opens a possibility of the effective synthesis on their basis of new β-amino-functionalized organophosphorus compounds. The latter are promising for the use as biologically active compounds, metal extractants, and membrane carriers [1–3]. In this work the results of the study of the reaction between 3-methyl-1,2-butadienylphosphonates I and 4,9-dioxa-1,12-dodecanediamine II are presented. On mixing diamine II with two-fold excess of phosphonate I the oily adduct III was obtained. It was washed with СН2Cl2 to the constant value of nD. In the IR spectra of compound III the stretching vibrations band of allene triad (1955 cm) is absent, and strong bands at 1200 (Р=О), 1590 (С=С), 3300– 3500 cm (NH) appear. The absence of the proton signals of phosphorus methylene group with the spinspin coupling constant JPH 20–22 Hz and of the proton signals of two methyl groups at the double bond makes it possible to ascribe to compounds IIIа and IIIb the enamine structure. Compounds IIIа and IIIb possess effective antimycotic activity.