Study On The Synthesis Of Halo Derivatives Of Adamantane

Halogenated adamantine derivatives are the important intermediates of polynitroadamantane.Therefore,it is important and valuable to study on the synthesis of halogenated adamantine derivatives.Octchloroadamantanecarboxylic acid was synthesized under ultraviole(UV)using1-carboxyadamantane as raw material.The products were characterized by melting point,IR,MS,DSC and13 C NMR.The results showed that octchloroadamantanecarboxylic acid was prepared successfully.The influences on the yield of crude products were studied,such as the UV light source,the rate of chlorine gas,et al.Through single factor experiments.the best reaction condition was determined.Furemore,the purification of the target product was studied.The geometric structures of the isomers of octchloroadamantanecarboxylic were fully optimized by B3LYP/6-311++G** method based on density functional theory.1,3,5,7-tetrachloroadamantane was synthesized under UV using adamantane as raw material,and carbon tetrachloride as solvent.The products were characterized by melting point,IR,and1 H NMR.The results showed that 1,3,5,7-tetrachloroadamantane was prepared successfully and the pattern like snowflakes.The effects of the different UV light sources and sublimation temperatures on the yield were studied,and the product was purified by controlling sublimation temperature.This process had more advantages than the traditional.such as mild reaction conditions,green chemistry environment-friendly and short reaction time.Adamantyl nitrates derivatives was synthesized by Victor-Meyer reaction using oct-chloroadamantanecarboxyli,1,3,5,7-tetrachloroadamantane and 1,3,5,7-tetrabromoadaman-tane as raw material.The products were characterized by melting point,MS and IR.The result showed that the new substances were obtained but not pure.The geometric structure of 1,3,5,7-tetranitroxyadamantane and 3,5,7-trianitroxyadamantane-1-carboxylicacid were optimized by B3LYP/6-311++G** method based on density functional theory.The detonation performance of target compounds were calculated by Kamlet-Jacobs equation,and the result were 1.67g/cm3,8.06km/s,25.52 GPa of 3,5,7-trianitroxyadam antane-1-carboxylic acid,1.67g/cm3,8.06km/s,25.52 GPa of 1,3,5,7-tetranitr-oxyadaman tane.