Chemical Society Reviews, volume 28, issue 1, pages 25-35
Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry
Publication type: Journal Article
Publication date: 1999-01-01
Journal:
Chemical Society Reviews
Q1
Q1
SJR: 12.511
CiteScore: 80.8
Impact factor: 40.4
ISSN: 03060012, 14604744
DOI:
10.1039/a804291h
General Chemistry
Abstract
The rates and selectivities of the hydrogen-atom abstraction reactions of electrically-neutral free radicals are known to depend on polar effects which operate in the transition state. Thus, an electrophilic species such as an alkoxyl radical abstracts hydrogen much more readily from an electron-rich C–H bond than from an electron-deficient one of similar strength. The basis of polarity-reversal catalysis (PRC) is to replace a single-step abstraction, that is slow because of unfavourable polar effects, with a two-step process in which the radicals and substrates are polarity-matched. This review explores the concept of PRC and describes its application in a variety of situations relevant to mechanistic and synthetic organic chemistry.
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Roberts B. P. Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry // Chemical Society Reviews. 1999. Vol. 28. No. 1. pp. 25-35.
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Roberts B. P. Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry // Chemical Society Reviews. 1999. Vol. 28. No. 1. pp. 25-35.
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RIS
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TY - JOUR
DO - 10.1039/a804291h
UR - https://doi.org/10.1039/a804291h
TI - Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry
T2 - Chemical Society Reviews
AU - Roberts, Brian P.
PY - 1999
DA - 1999/01/01
PB - Royal Society of Chemistry (RSC)
SP - 25-35
IS - 1
VL - 28
SN - 0306-0012
SN - 1460-4744
ER -
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BibTex (up to 50 authors)
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@article{1999_Roberts,
author = {Brian P. Roberts},
title = {Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry},
journal = {Chemical Society Reviews},
year = {1999},
volume = {28},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://doi.org/10.1039/a804291h},
number = {1},
pages = {25--35},
doi = {10.1039/a804291h}
}
Cite this
MLA
Copy
Roberts, Brian P.. “Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry.” Chemical Society Reviews, vol. 28, no. 1, Jan. 1999, pp. 25-35. https://doi.org/10.1039/a804291h.