1,1,4,4-TETRANITROBUTANE-2,3-DIOL AND ITS DERIVATIVES .2. CHLORINATION AND BROMINATION OF 1,1,4,4-TETRANITROBUTANE-2,3-DIOL - CRYSTAL-STRUCTURE OF HALOGEN-DERIVATIVES OF 1,1,4,4-TETRANITROBUTANE-2,3-DIOL

The bromination of 1,1,4,4-tetranitrobutane-2,3-diol in 60% acetic acid gave 1,4-dibromo-1,1,4,4-tetranitrobutane-2,3-diol in satisfactory yield. The chlorination of 1,1,4,4-tetranitrobutane-2,3-diol under analogous conditions gave 1,4-dichloro-1,1,4,4-tetranitrobutane-2,3-diol as a crystal hydrate. Drying of this latter product in vacuum over phosphorus pentoxide gave 1,4-dichloro-1,1, 4,4-tetranitrobutane-2,3-diol in quantitative yield. The structures of these products were determined by x-ray diffraction structural analysis. The crystal chemical analysis and quantum chemical calculations established an increase in secondary oxygen-halogen interactions in the halodinitromethyl fragment with increasing atomic number of the halogen atom.