3-Hydroxy pyrroles and 1H-Pyrrol-3(2H)-ones. Part 4. Oxidation of 2-Monosubstituted and 2-Unsubstituted pyrrolones, with an electron spin resonance study of a dimeric intermediate

Hamish McNab; Lilian C. Monahan; John C. Walton

doi:10.1039/P29880000759

3-Hydroxy pyrroles and 1H-Pyrrol-3(2H)-ones. Part 4. Oxidation of 2-Monosubstituted and 2-Unsubstituted pyrrolones, with an electron spin resonance study of a dimeric intermediate

Hamish McNab^*, Lilian C. Monahan, John C. Walton

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Oxidation of 2-substituted 1 H-pyrrol-3(2H)-ones in air gives 2-hydroxy derivatives, which can exist in solvent-dependent equilibrium with open-chain acyl enaminones. Oxidation of 2-unsubstitued analogues by irradiation in the presence of di-t-butyl peroxide gives rise to persistent radicals, identified as pyrrolone dimers [e.g. (21)] by e.s.r. spectroscopy. The formation of the various products is rationalised by a single mechanism (Scheme 3) in which a capto-dative radical (22) is a key intermediate.

Original language	English
Pages (from-to)	759-764
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	5
DOIs	https://doi.org/10.1039/P29880000759
Publication status	Published - 1 Jan 1988

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title = "3-Hydroxy pyrroles and 1H-Pyrrol-3(2H)-ones. Part 4. Oxidation of 2-Monosubstituted and 2-Unsubstituted pyrrolones, with an electron spin resonance study of a dimeric intermediate",

abstract = "Oxidation of 2-substituted 1 H-pyrrol-3(2H)-ones in air gives 2-hydroxy derivatives, which can exist in solvent-dependent equilibrium with open-chain acyl enaminones. Oxidation of 2-unsubstitued analogues by irradiation in the presence of di-t-butyl peroxide gives rise to persistent radicals, identified as pyrrolone dimers [e.g. (21)] by e.s.r. spectroscopy. The formation of the various products is rationalised by a single mechanism (Scheme 3) in which a capto-dative radical (22) is a key intermediate.",

author = "Hamish McNab and Monahan, {Lilian C.} and Walton, {John C.}",

year = "1988",

month = jan,

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doi = "10.1039/P29880000759",

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pages = "759--764",

journal = "Journal of the Chemical Society, Perkin Transactions 2",

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3-Hydroxy pyrroles and 1H-Pyrrol-3(2H)-ones. Part 4. Oxidation of 2-Monosubstituted and 2-Unsubstituted pyrrolones, with an electron spin resonance study of a dimeric intermediate. / McNab, Hamish; Monahan, Lilian C.; Walton, John C.
In: Journal of the Chemical Society, Perkin Transactions 2, No. 5, 01.01.1988, p. 759-764.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 3-Hydroxy pyrroles and 1H-Pyrrol-3(2H)-ones. Part 4. Oxidation of 2-Monosubstituted and 2-Unsubstituted pyrrolones, with an electron spin resonance study of a dimeric intermediate

AU - McNab, Hamish

AU - Monahan, Lilian C.

AU - Walton, John C.

PY - 1988/1/1

Y1 - 1988/1/1

N2 - Oxidation of 2-substituted 1 H-pyrrol-3(2H)-ones in air gives 2-hydroxy derivatives, which can exist in solvent-dependent equilibrium with open-chain acyl enaminones. Oxidation of 2-unsubstitued analogues by irradiation in the presence of di-t-butyl peroxide gives rise to persistent radicals, identified as pyrrolone dimers [e.g. (21)] by e.s.r. spectroscopy. The formation of the various products is rationalised by a single mechanism (Scheme 3) in which a capto-dative radical (22) is a key intermediate.

AB - Oxidation of 2-substituted 1 H-pyrrol-3(2H)-ones in air gives 2-hydroxy derivatives, which can exist in solvent-dependent equilibrium with open-chain acyl enaminones. Oxidation of 2-unsubstitued analogues by irradiation in the presence of di-t-butyl peroxide gives rise to persistent radicals, identified as pyrrolone dimers [e.g. (21)] by e.s.r. spectroscopy. The formation of the various products is rationalised by a single mechanism (Scheme 3) in which a capto-dative radical (22) is a key intermediate.

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JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

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ER -

3-Hydroxy pyrroles and 1H-Pyrrol-3(2H)-ones. Part 4. Oxidation of 2-Monosubstituted and 2-Unsubstituted pyrrolones, with an electron spin resonance study of a dimeric intermediate

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