Is there Ring–Chain Tautomerism in γ-Nitrosoalkanols?

γ-Nitrosoalkanols 2, 6 and 8, obtained upon acid hydrolysis of 2-methoxyisoxazolidines 1 and 7 and of dimethoxyamine 5, respectively, do not display ring–chain tautomerism, i.e. formation of the corresponding 2-hydroxyisoxazolidines (‘heminitrosals’); nitrosoalkanol 2 smoothly rearranges to oxime 4, whilst compound 8 in MeOH gives diol 9, probably via aerial oxidation to the corresponding nitrite followed by denitrosation.