A novel synthesis of adamantane polyhydric alcohols by direct oxidation of adamantane

Adamantane polyhydric alcohols are important active intermediates for synthesis of adamantane-based specific medicines,fine chemicals and functional materials.In this paper,three adamantane polyhydric alcohols,including adamantane-1,3-diol,adamantane-1,3,5-triol and adamantane-1,3,5,7-tetraol were synthesized via one-step oxidation reaction of adamantane by using Cr(Ⅵ)reagents as oxidants,acetic acid as solvent under the mild conditions.The structures of adamantane-1,3-diol,adamantane-1,3,5-triol and adamantane-1,3,5,7-tetraol were confirmed by IR,1H NMR and element analysis.Influences of synthesis conditions on the oxidation reaction were investigated.The reaction mechanism of adamantane oxidation by Cr(Ⅵ)reagents was discussed as well.Under the optimum conditions,adamantane-1,3-diol,adamantane-1,3,5-triol and adamantane-1,3,5,7-tetraol could be synthesized with the yields of 71%,42% and 35% respectively.Such synthesis technology for adamantane polyhydric alcohols is of potential for application because of brief reaction,convenient manipulation,and the mild conditions and so on.