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.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2372–2380, October, 1991.