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The pyridine denitration of cis- and trans-1, 2-cyclohexanediol dinitrates. Zane, Alexis


Refluxing cis- and trans-1,2-cyclohexanediol dinitrates in excess anhydrous pyridine at 118°-120°C lead to a slow decomposition of the dinitrates and the < formation of a gaseous product. It was found that the trans-dinitrate decomposed 1.8 times faster than the cis-isomer, and that no 2-nitroxycyclohexanols or 1,2- cyclohexanediols were formed. Nine components were detected in the reaction mixture by paper chromatography. Pyridinium nitrate, succinic and adipic acids, and a polymer were shown to be produced in the trans-denitration mixture. The use of 3-methylheptane in place of pyridine as solvent gave the decomposition products: oxalic, succinic and adipic acids, water, carbonized material, a reddish-brown gas and unsaturated compounds. The reaction of quinoline with the trans-dinitrate at 165° C yielded mainly water and a pyridine soluble polymer.

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