REACTIONS OF NUCLEOPHILIC-SUBSTITUTION INVOLVING SOLID ORGANIC HALOGEN COMPOUNDS UNDER SHEAR DEFORMATION AT HIGH-PRESSURE

Under conditions of shear deformation and high pressures (SD+HP), reac tions of nucleophilic substitution were studied: 1) the replacement of aliphatic halogen atom with alkaline metal halides (halo-substituted aliphatic carboxylic acids, 1-bromoadamantane); 2) the replacement of halogen atom in aromatic nucleus (halobenzoic acids, dihalobenzenes) w ith halogen of salt; 3) the replacement of aliphatic halogen with hydr oxyl (hydrolysis in a solid phase); 4) the replacement of halogen with amino group under deformation of the samples of ammonium alpha-haloca rboxylates to give the corresponding amino acids. It was found that th e exchange of the halogen atoms bonded with aliphatic carbon is most i ntensive in the mixtures of alkaline metal iodides with bromo-substitu ted acetic and propionic acids: the exchange reaction in these mixture s is observed even during grinding in the mortar. Unlike the liquid ph ase, under conditions of SD+HP exchange of the halogen atom of the aro matic nucleus with alkaline metal halides, proceeds successfully, and the reactivity of halides increases in the series Na < K < Rb < Cs. Un der SD+HP, 1-Br-adamantane reacts with water to form 1-adamantanol. A high reactivity of the water adsorbed by the reagents is observed.