T. Shaekhov, E. Gibadullina, Y. K. Voronina
Dec 1, 2012
Citations
0
Influential Citations
1
Citations
Journal
Russian Chemical Bulletin
Abstract
While studing the synthesis and properties of phospho rylated methylenequinones,1—5 we have accessed dibutyl (3,5 di tert butyl 4 oxo 2,5 cyclohexadienylidenemeth yl)phosphonate (1) by oxidation of dibutyl (3,5 di tert butyl 4 hydroxybenzyl)phosphonate (2) with alkaline po tassium ferrihexacyanide (Scheme 1). The structure and composition of compound 1 were established based on the 1H, 31P NMR and IR spectro scopic data, mass spectrometric (MALDI) data, and ele mental analysis. We found that with time compound 1 undergoes dimerization leading to 1,2 bis(dibutoxyphos phoryl) 1,2 bis(3,5 di tert butyl 4 hydroxyphenyl)ethane (3). The process reached completion within 10 days, which was indicated by the disappearance in the 31P NMR spec trum of the signal for the starting compound 1 (P 15.0) and the presence of the only singlet for the dimerization product 3 (P 27.5). The structure and composition of compound 3 were confirmed by the 1H, 31P NMR and IR spectroscopic data, mass spectrometric (MALDI) data, elemental analysis, and X ray diffraction studies (Fig. 1). It should be noted that in the solution in benzene, methylenequinone 1 did not undergo visible changes over prolonged period of time.