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John M. D. Storey

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Organization: University of Aberdeen , England
Department: Department of Chemistry
Title: (PhD)
Synthesis using aromatic homolytic substitution—recent advances
Co-reporter:W. Russell Bowman and John M. D. Storey  
Chemical Society Reviews 2007 vol. 36(Issue 11) pp:1803-1822
Publication Date(Web):05 Jul 2007
DOI:10.1039/B605183A
This critical review aims at presenting recent developments in intramolecular aromatic homolytic substitution which has become one of the common methodologies in modern synthesis. The application of Bu3SnH-mediated cyclisations have proved especially useful. The critical review illustrates the mechanistic considerations required for planning synthetic applications and a wide range of synthetic protocols and natural product syntheses are shown. The latest evidence for the mechanisms involved in aromatic homolytic substitution are presented. (152 references).
The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution
Co-reporter:Athelstan L. J. Beckwith ;Vincent W. Bowry Dr.;W. Russell Bowman ;Emma Mann Dr.;Jonathan Parr Dr. Dr.
Angewandte Chemie International Edition 2004 Volume 43(Issue 1) pp:
Publication Date(Web):17 DEC 2003
DOI:10.1002/anie.200352419

The fate of intermediate π radicals is crucial in Bu3SnH-mediated cyclization by homolytic aromatic substitution, for example, of bromo compound 1 via radical 2 to give oxindole 3 (AIBN=azobisisobutyronitrile). The results indicate that the mechanism requires the abstraction of a hydrogen radical from the intermediate π radical by the radical initiator or a product of initiator breakdown, and also that arene solvents are not always the best solvents for radical reactions.

The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution
Co-reporter:Athelstan L. J. Beckwith ;Vincent W. Bowry Dr.;W. Russell Bowman ;Emma Mann Dr.;Jonathan Parr Dr. Dr.
Angewandte Chemie 2004 Volume 116(Issue 1) pp:
Publication Date(Web):17 DEC 2003
DOI:10.1002/ange.200352419

Das Schicksal intermediärer π-Radikale ist entscheidend bei der Bu3SnH-vermittelten Cyclisierung durch radikalische aromatische Substitution. So lagert sich die Bromverbindung 1 über das Radikal 2 in das Oxindol 3 um (AIBN=Azobisisobutyronitril). Dabei ist die Abspaltung des H-Atoms von der π-radikalischen Zwischenstufe durch den Radikalstarter ein wichtiger Schritt im Mechanismus. Die Ergebnisse zeigen, dass aromatische Lösungsmittel nicht immer das Solvens der Wahl für Radikalreaktionen sind.

Synthesis using aromatic homolytic substitution—recent advances
Co-reporter:W. Russell Bowman and John M. D. Storey
Chemical Society Reviews 2007 - vol. 36(Issue 11) pp:NaN1822-1822
Publication Date(Web):2007/07/05
DOI:10.1039/B605183A
This critical review aims at presenting recent developments in intramolecular aromatic homolytic substitution which has become one of the common methodologies in modern synthesis. The application of Bu3SnH-mediated cyclisations have proved especially useful. The critical review illustrates the mechanistic considerations required for planning synthetic applications and a wide range of synthetic protocols and natural product syntheses are shown. The latest evidence for the mechanisms involved in aromatic homolytic substitution are presented. (152 references).
Cyclopropanecarbonyl chloride, 1-bromo-
Cyclopropanecarbonyl chloride, 1-bromo-
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Phenol, 2-bromo-3-(2-propenyloxy)-
Phenol, 2-bromo-3-(2-propenyloxy)-
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Phenol, 2-bromo-3-(2-propenyloxy)-
2H-Imidazole-2-thione, 1,3-dihydro-1-methyl-3-(2-phenylethyl)-
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2-Butenenitrile, 4-bromo-
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Methyl, (4-methoxyphenyl)-
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SPIRO[CYCLOHEXANE-1,3'-[3H]PYRROLO[3,2-C]PYRIDIN]-2'(1'H)-ONE, 1'-METHYL-
SPIRO[CYCLOHEXANE-1,3'-[3H]PYRROLO[3,2-C]PYRIDIN]-2'(1'H)-ONE, 1'-METHYL-
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SPIRO[CYCLOHEXANE-1,3'-[3H]PYRROLO[3,2-C]PYRIDIN]-2'(1'H)-ONE, 1'-METHYL-
SPIRO[CYCLOBUTANE-1,3'-[3H]PYRROLO[3,2-C]PYRIDIN]-2'(1'H)-ONE, 1'-METHYL-
SPIRO[CYCLOBUTANE-1,3'-[3H]PYRROLO[3,2-C]PYRIDIN]-2'(1'H)-ONE, 1'-METHYL-
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SPIRO[CYCLOBUTANE-1,3'-[3H]PYRROLO[3,2-C]PYRIDIN]-2'(1'H)-ONE, 1'-METHYL-
2-BUTENENITRILE, 4-[2-BROMO-3-(2-PROPENYLOXY)PHENOXY]-, (2E)-
2-BUTENENITRILE, 4-[2-BROMO-3-(2-PROPENYLOXY)PHENOXY]-, (2E)-
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BENZENE, 2-BROMO-1-[[(2E)-3-PHENYL-2-PROPENYL]OXY]-3-(2-PROPENYLOXY)-
BENZENE, 2-BROMO-1-[[(2E)-3-PHENYL-2-PROPENYL]OXY]-3-(2-PROPENYLOXY)-
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BENZENE, 2-BROMO-1-[[(2E)-3-PHENYL-2-PROPENYL]OXY]-3-(2-PROPENYLOXY)-