A New Synthesis of Alkyl Nitrites: The Reaction of Alkyl Alcohols with Nitric Oxide in Organic Solvents.

In a nonaqueous solvent, alkyl nitrites can be easily achieved through the reaction of alkyl alcohols and gaseous NO. In the presence of air, the nitric oxide can in fact be oxidized to nitrous anhydride, which acts as a nitrosating agent. A quantitative study conducted on cycloalkyl alcohols has shown conversion yields to nitrites within the range 65-90%. This result has been validated by ESR spectroscopy experiments on several alkyl alcohols/NO mixtures, which lead to the detection of the same radical species detectable when a solution of the corresponding nitrites is photolyzed.