One-Electron Oxidation of 2-(4-Methoxyphenyl)-2-Methylpropanoic and 1-(4-Methoxyphenyl)cyclopropanecarboxylic Acids in Aqueous Solution. The Involvement of Radical Cations and the Influence of Structural Effects and pH on the Side-Chain Fragmentation Reactivity

Massimo Bietti; Alberto Capone

doi:10.1021/jo702104j

One-Electron Oxidation of 2-(4-Methoxyphenyl)-2-Methylpropanoic and 1-(4-Methoxyphenyl)cyclopropanecarboxylic Acids in Aqueous Solution. The Involvement of Radical Cations and the Influence of Structural Effects and pH on the Side-Chain Fragmentation Reactivity

The Journal of Organic Chemistry ◽

10.1021/jo702104j ◽

2008 ◽

Vol 73 (2) ◽

pp. 618-629 ◽

Cited By ~ 5

Author(s):

Massimo Bietti ◽

Alberto Capone

Keyword(s):

Aqueous Solution ◽

Radical Cations ◽

Side Chain ◽

Structural Effects

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Oxygen Versus Carbon Acidity in the Side-Chain Fragmentation of 2-, 3-, and 4-Arylalkanol Radical Cations in Aqueous Solution: The Influence of the Distance between the OH Group and the Aromatic Ring1

Journal of the American Chemical Society ◽

10.1021/ja990352+ ◽

1999 ◽

Vol 121 (28) ◽

pp. 6624-6629 ◽

Cited By ~ 12

Author(s):

Enrico Baciocchi ◽

Massimo Bietti ◽

Laura Manduchi ◽

Steen Steenken

Keyword(s):

Aqueous Solution ◽

Radical Cations ◽

Side Chain

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−OH-Induced shift from carbon to oxygen acidity in the side-chain deprotonation of 2-, 3- and 4-methoxybenzyl alcohol radical cations in aqueous solution: results from pulse radiolysis and DFT calculations

Tetrahedron ◽

10.1016/s0040-4020(02)01585-5 ◽

2003 ◽

Vol 59 (5) ◽

pp. 613-618 ◽

Cited By ~ 8

Author(s):

Enrico Baciocchi ◽

Massimo Bietti ◽

Gianfranco Ercolani ◽

Steen Steenken

Keyword(s):

Aqueous Solution ◽

Dft Calculations ◽

Pulse Radiolysis ◽

Radical Cations ◽

Side Chain ◽

Alcohol Radical

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Reactivity and Acid−Base Behavior of Ring-Methoxylated Arylalkanoic Acid Radical Cations and Radical Zwitterions in Aqueous Solution. Influence of Structural Effects and pH on the Benzylic C−H Deprotonation Pathway†

The Journal of Organic Chemistry ◽

10.1021/jo060678i ◽

2006 ◽

Vol 71 (14) ◽

pp. 5260-5267 ◽

Cited By ~ 4

Author(s):

Massimo Bietti ◽

Alberto Capone

Keyword(s):

Aqueous Solution ◽

Radical Cations ◽

Structural Effects ◽

Acid Base ◽

Acid Radical

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Structural Effects on the OH−-Promoted Fragmentation of Methoxy-Substituted 1-Arylalkanol Radical Cations in Aqueous Solution: The Role of Oxygen Acidity

Chemistry - A European Journal ◽

10.1002/1521-3765(20010401)7:7<1408::aid-chem1408>3.0.co;2-m ◽

2001 ◽

Vol 7 (7) ◽

pp. 1408-1416 ◽

Cited By ~ 8

Author(s):

Enrico Baciocchi ◽

Massimo Bietti ◽

Maria Francesca Gerini ◽

Laura Manduchi ◽

Michela Salamone ◽

...

Keyword(s):

Aqueous Solution ◽

Radical Cations ◽

Structural Effects ◽

Substituted 1

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Kinetic and Product Studies on the Side-Chain Fragmentation of 1-Arylalkanol Radical Cations in Aqueous Solution: Oxygen versus Carbon Acidity

Chemistry - A European Journal ◽

10.1002/(sici)1521-3765(19990604)5:6<1785::aid-chem1785>3.0.co;2-0 ◽

1999 ◽

Vol 5 (6) ◽

pp. 1785-1793 ◽

Cited By ~ 18

Author(s):

Enrico Baciocchi ◽

Massimo Bietti ◽

Steen Steenken

Keyword(s):

Aqueous Solution ◽

Radical Cations ◽

Side Chain

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Side-chain oxidation of some phenyl-substituted alcohols in aqueous solution: Formation and fragmentation of radical-cations

Research on Chemical Intermediates ◽

10.1007/bf03051814 ◽

1989 ◽

Vol 11 (1) ◽

pp. 1-17 ◽

Cited By ~ 9

Author(s):

B. C. Gilbert ◽

C. J. Warren

Keyword(s):

Aqueous Solution ◽

Radical Cations ◽

Side Chain ◽

Chain Oxidation ◽

Solution Formation

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Inter- and intra-molecular radical cations of alkyl bromides in aqueous solution

Chemical Physics Letters ◽

10.1016/0009-2614(92)85755-y ◽

1992 ◽

Vol 194 (1-2) ◽

pp. 135-138 ◽

Cited By ~ 7

Author(s):

H. Mohan ◽

D.K. Maity ◽

J.P. Mittal

Keyword(s):

Aqueous Solution ◽

Radical Cations ◽

Alkyl Bromides ◽

Molecular Radical

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Thermal decomposition of peroxydisulfate in aqueous solution of benzene-nitrobenzene-benzonitrile mixtures. Formation of OH radicals from benzene radical cations and water at room temperature

Journal of the American Chemical Society ◽

10.1021/ja00389a031 ◽

1982 ◽

Vol 104 (25) ◽

pp. 7069-7073 ◽

Cited By ~ 12

Author(s):

Manfred K. Eberhardt ◽

Gines A. Martinez ◽

Juana I. Rivera ◽

Anselmo Fuentes-Aponte

Keyword(s):

Aqueous Solution ◽

Thermal Decomposition ◽

Room Temperature ◽

Radical Cations ◽

Oh Radicals

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Electron spin resonance studies. Part 58. The formation and reactions of some aliphatic radical-cations in aqueous solution

Journal of the Chemical Society Perkin Transactions 2 ◽

10.1039/p29800000647 ◽

1980 ◽

pp. 647 ◽

Cited By ~ 25

Author(s):

Bruce C. Gilbert ◽

Richard O. C. Norman ◽

Peter S. Williams

Keyword(s):

Aqueous Solution ◽

Electron Spin Resonance ◽

Electron Spin ◽

Radical Cations ◽

Spin Resonance ◽

Aliphatic Radical

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Der Einfluß der Struktur polyoxypropylierter sekundärer Amine auf ihre Adsorption an der Grenzfläche Wäßrige Lösung-Luft / Structural Effects of Polyoxypropylated Secondary Amines on their Adsorption at the Aqueous Solution - Air Interface

Tenside Surfactants Detergents ◽

10.1515/tsd-1991-280419 ◽

1991 ◽

Vol 28 (4) ◽

pp. 267-272

Author(s):

A. Sokolowski ◽

J. Chlebicki ◽

K. A. Wilk

Keyword(s):

Aqueous Solution ◽

Secondary Amines ◽

Structural Effects ◽

Air Interface

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