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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

Dobmeier, Michael, Herrmann, Josef M., Lenoir, Dieter and 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, pp. 330-336.

Date of publication of this fulltext: 08 Mar 2012 07:29
Article
DOI to cite this document: 10.5283/epub.23539


Abstract

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

Item typeArticle
Journal or Publication TitleBeilstein Journal of Organic Chemistry
Publisher:BEILSTEIN-INSTITUT
Place of Publication:FRANKFURT AM MAIN
Volume:8
Page Range:pp. 330-336
Date2012
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Identification Number
ValueType
10.3762/bjoc.8.36DOI
KeywordsHYPOPHOSPHOROUS ACID; INDUCED DEOXYGENATION; ORGANOTIN COMPOUNDS; ALLYLIC ALCOHOLS; HYDROGEN IODIDE; REDUCING SYSTEM; DERIVATIVES; PHOSPHORUS; PHOSPHITES; SECONDARY;
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-235396
Item ID23539

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