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Quantitating the effect of an ortho substituent on cyclization and intramolecular hydrogen-transfer reactions of aryl radicals

Curran, DP and Fairweather, N (2003) Quantitating the effect of an ortho substituent on cyclization and intramolecular hydrogen-transfer reactions of aryl radicals. Journal of Organic Chemistry, 68 (7). 2972 - 2974. ISSN 0022-3263

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Abstract

Reduction of allyl 2-iodobenzyl malonates with triphenyltin hydrides generates aryl radicals that partition between 6-exo cyclization, 7-endo cyclization, and 1,5-hydrogen atom transfer. Rate constants for all of these processes are high (> 108 M-1 s-1), and the rates are only marginally reduced (<33%) by the introduction of methyl group ortho to the reacting radical.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Fairweather, N
Date: 4 April 2003
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 68
Number: 7
Page Range: 2972 - 2974
DOI or Unique Handle: 10.1021/jo0268759
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Alkylation; Catalysis; Cyclization; Hydrocarbons, Cyclic--chemistry; Hydrogen--chemistry; Indicators and Reagents; Kinetics; Malonates--chemistry; Methylation; Molecular Structure
PubMed ID: 12662080
Date Deposited: 31 Jan 2014 21:07
Last Modified: 22 Jun 2021 12:56
URI: http://d-scholarship.pitt.edu/id/eprint/20449

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