The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution

Athelstan L.J. Beckwith; Vincent W. Bowry; W. Russell Bowman; Emma Mann; Jonathan Parr; John M.D. Storey

doi:10.1002/anie.200352419

The Mechanism of Bu₃SnH-Mediated Homolytic Aromatic Substitution

Athelstan L.J. Beckwith^*, Vincent W. Bowry, W. Russell Bowman, Emma Mann, Jonathan Parr, John M.D. Storey

^*Corresponding author for this work

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

118 Citations (Scopus)

Abstract

The fate of intermediate π radicals is crucial in Bu ₃SnH-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.

Original language	English
Pages (from-to)	95-98
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	1
DOIs	https://doi.org/10.1002/anie.200352419
Publication status	Published - 22 Dec 2004

Access to Document

10.1002/anie.200352419

Cite this

@article{4e861cc4ae264bfdb16369c4fef6cedb,

title = "The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution",

abstract = "The fate of intermediate π radicals is crucial in Bu 3SnH-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.",

keywords = "Azo compounds, Cyclization, Radical reactions, Radicals, Reaction mechanisms",

author = "Beckwith, {Athelstan L.J.} and Bowry, {Vincent W.} and Bowman, {W. Russell} and Emma Mann and Jonathan Parr and Storey, {John M.D.}",

year = "2004",

month = dec,

day = "22",

doi = "10.1002/anie.200352419",

language = "English",

volume = "43",

pages = "95--98",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley & Sons Ltd.",

number = "1",

}

TY - JOUR

T1 - The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution

AU - Beckwith, Athelstan L.J.

AU - Bowry, Vincent W.

AU - Bowman, W. Russell

AU - Mann, Emma

AU - Parr, Jonathan

AU - Storey, John M.D.

PY - 2004/12/22

Y1 - 2004/12/22

N2 - The fate of intermediate π radicals is crucial in Bu 3SnH-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.

AB - The fate of intermediate π radicals is crucial in Bu 3SnH-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.

KW - Azo compounds

KW - Cyclization

KW - Radical reactions

KW - Radicals

KW - Reaction mechanisms

UR - http://www.scopus.com/inward/record.url?scp=2442630750&partnerID=8YFLogxK

U2 - 10.1002/anie.200352419

DO - 10.1002/anie.200352419

M3 - Article

SN - 1433-7851

VL - 43

SP - 95

EP - 98

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 1

ER -

The Mechanism of Bu₃SnH-Mediated Homolytic Aromatic Substitution

Abstract

Access to Document

Other files and links

Fingerprint

Cite this