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Do alpha-acyloxy and alpha-alkoxycarbonyloxy radicals fragment to form acyl and alkoxycarbonyl radicals?

Curran, DP and Turner, TR (2006) Do alpha-acyloxy and alpha-alkoxycarbonyloxy radicals fragment to form acyl and alkoxycarbonyl radicals? Beilstein Journal of Organic Chemistry, 2. ISSN 1860-5397

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Abstract

The generation of α-acyloxy and α-alkoxycarbonyloxy radicals under reductive conditions in fragmentable probe experiments does not provide unequivocal evidence for the fragmentation of such radicals to give ketones and acyl or alkoxycarbonyl radicals. Instead, standard reduction predominates, even at low tin hydride concentrations. Some ketone product is formed in the α-acyloxy substrate at low concentrations, but it is unclear whether this product arises through a slow radical fragmentation process or an inefficient, chain-breaking oxidative process. © 2006 Curran and Turner; licensee Beilstein-Institut.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Turner, TR
Date: 25 May 2006
Date Type: Publication
Journal or Publication Title: Beilstein Journal of Organic Chemistry
Volume: 2
DOI or Unique Handle: 10.1186/1860-5397-2-10
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1860-5397
Other ID: NLM PMC1524793
PubMed Central ID: PMC1524793
PubMed ID: 16725051
Date Deposited: 07 Jun 2013 19:57
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/18883

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