1965•Canadian Journal of ChemistryOpen access

STUDIES IN THE PYRROLINE SERIES: V. 3,3-DIMETHYL-1-PYRROLINE-1-OXIDE

Raymond Bonnett, Suzzy C. Ho, James A. Raleigh

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Abstract

The pyrolysis of 1-ethyl-3,3-dimethylpyrrolidine-1-oxide gives 1-hydroxy-3,3-dimethylpyrrolidine, which, on dehydrogenation, yields 3,3-dimethyl-1-pyrroline-1-oxide. The identification of the nitrone is described. The cyclo-additions of styrene to this nitrone and to 5,5-dimethyl-1-pyrroline-1-oxide were investigated, and the direction of addition was deduced from the n.m.r. spectra of the adducts.

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The pyrolysis of 1-ethyl-3,3-dimethylpyrrolidine-1-oxide gives 1-hydroxy-3,3-dimethylpyrrolidine, which, on dehydrogenation, yields 3,3-dimethyl-1-pyrroline-1-oxide. The identification of the nitrone is described. The cyclo-additions of styrene to this nitrone and to 5,5-dimethyl-1-pyrroline-1-oxide were investigated, and the direction of addition was deduced from the n.m.r. spectra of the adducts.

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Available abstract

The pyrolysis of 1-ethyl-3,3-dimethylpyrrolidine-1-oxide gives 1-hydroxy-3,3-dimethylpyrrolidine, which, on dehydrogenation, yields 3,3-dimethyl-1-pyrroline-1-oxide. The identification of the nitrone is described. The cyclo-additions of styrene to this nitrone and to 5,5-dimethyl-1-pyrroline-1-oxide were investigated, and the direction of addition was deduced from the n.m.r. spectra of the adducts.

Key concepts: Nitrone, Chemistry, Pyrroline, Dehydrogenation, Oxide, Styrene, Adduct, Pyrolysis

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