Diethylzinc: A Chain-Transfer Agent in Intermolecular Radical Additions. A Parallel with Triethylborane

In the presence of oxygen, diethylzinc can be used to promote radical additions to CN bond containing radical acceptors and to enones. In these reactions, it plays at the same time the role of the initiator and the role of the chain-transfer reagent. A parallel with triethylborane-mediated reaction...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 25; pp. 9189 - 9193
Main Authors Bertrand, Michèle P, Feray, Laurence, Nouguier, Robert, Perfetti, P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.12.1999
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
CARBON BOND FORMATION
N-(DIPHENYLPHOSPHINOYL) IMINES
ACYLATION APPROACH
ALKYL RADICALS
REACTIVITY
ENANTIOSELECTIVE ETHYLATION
DIALKYLZINC REAGENTS
GLYOXYLATE
OXIME ETHERS
ZINC
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Summary:In the presence of oxygen, diethylzinc can be used to promote radical additions to CN bond containing radical acceptors and to enones. In these reactions, it plays at the same time the role of the initiator and the role of the chain-transfer reagent. A parallel with triethylborane-mediated reactions is established. The methodology is restricted to secondary and tertiaryalkyl radicals generated from the corresponding alkyl iodides. It could not be extended either to CC bond containing radical acceptors such as methyl methacrylate and nitrocyclohexene or to diethylazodicarboxylate.
Bibliography:istex:6CE06D42BF78C13575387CA78E2E3DB634CF61C0
ark:/67375/TPS-0H7264JZ-B
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9912404