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Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium.
MedLine Citation:
PMID:  22423302     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Michael Dobmeier; Josef M Herrmann; Dieter Lenoir; Burkhard König
Publication Detail:
Type:  Journal Article     Date:  2012-03-02
Journal Detail:
Title:  Beilstein journal of organic chemistry     Volume:  8     ISSN:  1860-5397     ISO Abbreviation:  Beilstein J Org Chem     Publication Date:  2012  
Date Detail:
Created Date:  2012-03-16     Completed Date:  2012-08-23     Revised Date:  2013-05-29    
Medline Journal Info:
Nlm Unique ID:  101250746     Medline TA:  Beilstein J Org Chem     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  330-6     Citation Subset:  -    
Affiliation:
Institute of Organic Chemistry, University of Regensburg, D-93040 Regensburg, Germany.
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