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Reactivity of the ethyl oleate in the [3+2] cycloaddition to arylonitrile N-oxide: a reexamination

Dresler Ewa, Sadowski Mikołaj, Demchuk Oleg M.

Scientiae Radices

2024

Vol. 3, Iss. 2

108--121

The course of the reactions between ethyl oleate and aromatic nitrile N-oxides was reexamined under the laboratory conditions. The reaction course was explained on the basis of the DFT quantumchemical calculations. It was found that independently of the reaction protocol, in any case the expected 2-isoxazolines are not formed. Instead of this, respective diarylfuroxanes were isolated from post-reaction mixtures.

REaction of N-Arylbenzamidines with Arenenitrile N-Oxides

Szczepankiewicz W., Borowiak T., Kubicki M., Suwiński J., Wagner P.

Polish Journal of Chemistry

2002

Vol. 76 / nr 8

1137-1142

Looking for a method of 4-arylamino-4-aryl-3-aza-3-buten-2-one oximes preparation a reaction of N-arylbenzamidines with arenenitrile N-oxides (generated in situ form oximoyl chlorides) has been performed to produce unstable 5-amino-4,5-dihydro-1,2,4-oxadiazoles,which under aqueous acidic conditions hydrolyzed to acyclic N-benzoyloxy-N'-arylareneamidines. Structure of one of the latter compounds has been confirmed by X-ray analysis.