Interaction of 5,5-dimethyl-2-phenacylpyrroline-1-oxide — an exocyclic β-oxonitrone — with nucleophilic reagents

Authors

  • В. А. Резников Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • Л. Б. Володарский Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090

Abstract

A study has been made of the interaction of 2,5,5-trimethylpyrroline-1-oxide with ethyl formate, ethyl thiobenzoate, and methyl nitrate. It has been shown that the reaction of 5,5-dimethyl-2 phenacylpyrroline-1-oxide with methylmagnesium iodide or phenyllithium proceeds through the nitrone group, while the carbonyl group is preserved, after oxidation, this leads to nitroxyl radicals of the pyrrolidine series. Upon interaction of this same N-oxide with nitrogen-containing binucleophiles, recyclization takes place, forming derivatives of isoxazole and pyrazole.

How to Cite
Reznikov, V. A.; Volodarskii, L. B. Chem. Heterocycl. Compd. 1996, 32, 652. [Khim. Geterotsikl. Soedin. 1996, 760.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01164863

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Published

1996-06-25

Issue

No. 6 (1996)

Section

Original Papers