Photoreaction of nitroso compounds in solution. XIII. Photo-oxidation of alkyl nitrites

Photolysis of 1-pentyl and menthyl nitrites in the presence of oxygen were shown to give mainly the oxidized rearrangement products 4-nitratopentyl and 10-nitratomenthyl derivatives in disagreement with the published report (2). Under the photo-oxidation conditions, menthyl nitrite also gave 10-nitrosomenthyl derivatives which were also shown to be photo-oxidized to 10-nitratomenthyl derivatives. The photo-oxidation products were conveniently reduced to the corresponding diols and were, in turn, identified as bisbenzoate.