The rearrangements of the nitrones of simple cyclic conjugated ketones

Rolf H Prager; Kevin D Raner; A David Ward

doi:10.1071/CH9840381

The rearrangements of the nitrones of simple cyclic conjugated ketones

Rolf H Prager, Kevin D Raner, A David Ward

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15 Citations (Scopus)

Abstract

The ring expansions of N-methyl nitrones formed from cyclic conjugated ketones have been investigated. Low yields of cyclic amides were obtained. In general, the best conditions for the rearrangement involved using p-toluenesulfonyl chloride and polyphosphoric acid in tetrahydrofuran. The parent ketone and, in some cases, an N-aryl sulfonamide were also obtained; mechanisms for their formation are discussed.

Original language	English
Pages (from-to)	381-387
Number of pages	7
Journal	Australian Journal of Chemistry
Volume	37
Issue number	2
DOIs	https://doi.org/10.1071/CH9840381
Publication status	Published - 1984
Externally published	Yes

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title = "The rearrangements of the nitrones of simple cyclic conjugated ketones",

abstract = "The ring expansions of N-methyl nitrones formed from cyclic conjugated ketones have been investigated. Low yields of cyclic amides were obtained. In general, the best conditions for the rearrangement involved using p-toluenesulfonyl chloride and polyphosphoric acid in tetrahydrofuran. The parent ketone and, in some cases, an N-aryl sulfonamide were also obtained; mechanisms for their formation are discussed.",

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journal = "Australian Journal of Chemistry",

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AU - Raner, Kevin D

AU - Ward, A David

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AB - The ring expansions of N-methyl nitrones formed from cyclic conjugated ketones have been investigated. Low yields of cyclic amides were obtained. In general, the best conditions for the rearrangement involved using p-toluenesulfonyl chloride and polyphosphoric acid in tetrahydrofuran. The parent ketone and, in some cases, an N-aryl sulfonamide were also obtained; mechanisms for their formation are discussed.

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U2 - 10.1071/CH9840381

DO - 10.1071/CH9840381

M3 - Article

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VL - 37

SP - 381

EP - 387

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 2

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The rearrangements of the nitrones of simple cyclic conjugated ketones

Abstract

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