N,N-Dimethylformamide was found to act as solvent and catalyst in the dehydration of aldoximes to nitriles. The reaction required heating at 135 °C and yields of nitriles were moderate to good. (Benzylideneaminooxy)formaldehyde was detected as an intermediate in one of the reactions.

2-(Alkenyloxy)naphthalene-1-carbaldehyde oximes are oxidized with potassium iodide, iodine and sodium bicarbonate directly to novel naphthopyranoisoxazoles. Naphthopyranoisoxazoles are also prepared from 2-(3-chloroallyloxy)naphthalene-1carbaldehyde oxime or 2-(alkynyloxy)naphthalene-1-carbaldehyde oximes by oxidation with sodium hypochlorite and triethylamine. The oxidation of 2-(alkenyloxy)naphthalene-1-carbaldehyde oximes with sodium hypochlorite and triethylamine afforded novel naphthopyranoisoxazolines. The former reaction is tentatively proposed to occur via activation of the alkene side chain by means of an iodonium intermediate and either 1,3-dipolar interaction with a nitrile oxide side-group or cyclization with a hydroximic acid iodide side-group.

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Nitrile formation O 0273 DMF-Catalyzed Thermal Dehydration of Aldoximes: A Convenient Access to Functionalized Aliphatic and Aromatic Nitriles. -DMF acts as dehydrating agent and solvent. -(SUPSANA, P.; LIASKOPOULOS, T.; TSOUNGAS, P. G.; VARVOUNIS*, G.; Synlett 2007, 17, 2671-2674; Dep. Chem., Univ. Ioannina, GR-45110 Ioannina, Greece; Eng.) -Mais 09-054