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Dobmeier, Michael ; Herrmann, Josef M. ; Lenoir, Dieter ; König, Burkhard

Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium

Artikel

Dobmeier, Michael, Herrmann, Josef M., Lenoir, Dieter und König, Burkhard (2012) Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium. Beilstein Journal of Organic Chemistry 8, S. 330-336.

DOI zum Zitieren dieses Dokuments: 10.5283/epub.23539


Zusammenfassung

The synthetic protocol for the reduction of alcohols to hydrocarbons by using hydriodic acid, first described by Kiliani more than 140 years ago, was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene-water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields ...

The synthetic protocol for the reduction of alcohols to hydrocarbons by using hydriodic acid, first described by Kiliani more than 140 years ago, was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene-water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields and short reaction times, into the corresponding hydrocarbons. Red phosphorous was used as the stoichiometric reducing agent. Keto, ester, amide or ether groups are tolerated, and catalytic amounts of hydriodic acid (0.2 equiv) in the presence of 0.6 equiv phosphorous are sufficient to achieve conversion.



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Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftBeilstein Journal of Organic Chemistry
VerlagBEILSTEIN-INSTITUT
Ort der VeröffentlichungFRANKFURT AM MAIN
Band8
SeitenbereichS. 330-336
Datum2012
Veröffentlichungsdatum08 Mrz 2012 07:29
InstitutionenChemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Identifikationsnummer
WertTyp
10.3762/bjoc.8.36DOI
Stichwörter / KeywordsHYPOPHOSPHOROUS ACID; INDUCED DEOXYGENATION; ORGANOTIN COMPOUNDS; ALLYLIC ALCOHOLS; HYDROGEN IODIDE; REDUCING SYSTEM; DERIVATIVES; PHOSPHORUS; PHOSPHITES; SECONDARY;
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-235396
Dokumenten-ID23539

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