Preparation of Propargyl Hydroperoxides by Regioselective Oxidation of Allenic Zinc Reagents with Molecular Oxygen

Treatment of allenic zinc reagents (R1R2CCC(R3)ZnL), generated by the reaction of propargyl derivative (R1R2C(X)C⋮CH) with triorganozincates (R3 3ZnLi), under oxygen atmosphere in the presence of ZnCl2 and chlorotrimethylsilane afforded propargyl hydroperoxides (R1R2C(OOH)C⋮CR3) regioselectively....

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Bibliographic Details
Published inJournal of organic chemistry Vol. 68; no. 17; pp. 6716 - 6719
Main Authors Harada, Toshiro, Kutsuwa, Emiko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.08.2003
Amer Chemical Soc
Subjects
Aliphatic compounds
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
HOMOENOLATE
MAGNETIC RESONANCE SPECTRA
LITHIUM-7
ORGANOMETALLIC EXCHANGE REACTIONS
ETHER
ESTERS
Oxygen
Zinc II Chlorides
Acetylenic compound
Organic hydroperoxide
Regioselectivity
Propargylic compound
Oxidation
Chemical synthesis
Allenic compound
Lithium Zinc Organic compounds
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Summary:Treatment of allenic zinc reagents (R1R2CCC(R3)ZnL), generated by the reaction of propargyl derivative (R1R2C(X)C⋮CH) with triorganozincates (R3 3ZnLi), under oxygen atmosphere in the presence of ZnCl2 and chlorotrimethylsilane afforded propargyl hydroperoxides (R1R2C(OOH)C⋮CR3) regioselectively. In this reaction, the use of ZnCl2 and chlorotrimethylsilane as additives is essential for the transformation of the initially generated allenic reagents to more reactive chlorozinc species.
Bibliography:istex:8459EB8811016339EBFC9360EC8C7A11EFF1BC00
ark:/67375/TPS-SP5GN8T9-C
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo034743p