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1988•Australian Journal of ChemistryRequires access

Nitrones and Oxaziridines. XXXVII. Some Oxidation Reactions of 1-Pyrroline 1-Oxides

Dsc Black, RJ Strauch

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Abstract

The 2,4-diaryl-1-pyrroline 1-oxides (4) can be converted into the related 2H-pyrrole 1-oxides (5) by treatment with N-bromosuccinimide and anhydrous potassium carbonate. Similar treatment of the 1-pyrroline 1-oxide (6) yielded the succinimido-substituted pyrroline (7). Selenium dioxide oxidation of the tetramethyl nitrone (8) under various conditions gave mixtures containing the compounds (10)-(12). Neither process provides a general conversion of 1-pyrroline 1-oxides into 2H-pyrrole 1-oxides.

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What this paper is about

The 2,4-diaryl-1-pyrroline 1-oxides (4) can be converted into the related 2H-pyrrole 1-oxides (5) by treatment with N-bromosuccinimide and anhydrous potassium carbonate. Similar treatment of the 1-pyrroline 1-oxide (6) yielded the succinimido-substituted pyrroline (7). Selenium dioxide oxidation of the tetramethyl nitrone (8) under various conditions gave mixtures containing the compounds (10)-(12). Neither process provides a general conversion of 1-pyrroline 1-oxides into 2H-pyrrole 1-oxides.

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Available abstract

The 2,4-diaryl-1-pyrroline 1-oxides (4) can be converted into the related 2H-pyrrole 1-oxides (5) by treatment with N-bromosuccinimide and anhydrous potassium carbonate. Similar treatment of the 1-pyrroline 1-oxide (6) yielded the succinimido-substituted pyrroline (7). Selenium dioxide oxidation of the tetramethyl nitrone (8) under various conditions gave mixtures containing the compounds (10)-(12). Neither process provides a general conversion of 1-pyrroline 1-oxides into 2H-pyrrole 1-oxides.

Key concepts: Pyrroline, Chemistry, Nitrone, Green chemistry, Pyrrole, Biocatalysis, Potassium carbonate, Anhydrous

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