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Author Cook, G. K. ♦ Andrews, M. A.
Source United States Department of Energy Office of Scientific and Technical Information
Content type Text
Language English
Subject Keyword CHEMISTRY ♦ GLYCOLS ♦ CATALYSIS ♦ DEHYDRATION ♦ ALCOHOLS ♦ SYNTHESIS ♦ ALKENES ♦ RHENIUM COMPLEXES ♦ ORGANOMETALLIC COMPOUNDS ♦ POLYMERS
Abstract Carbohydrates, with one oxygen atom per carbon, are actually too oxygen-rich relative to many important oxygenated organics. Removal of carbohydrate hydroxyl groups would therefore be useful, particularly if a different reactive functional group could be introduced. This has now been accomplished via a new catalytic reaction, the stereospecific deoxydehydration of diols and polyols to alkenes and allylic alcohols. In summary, the present catalytic method for net didehydroxylation of diols is potentially competitive in many cases with the standard Corey-Winter approach, treatment of the diol thionocarbonate with phosphite reagents at elevated temperatures. Other metal diolate complexes are known to extrude alkene at room temperature. Hence we believe that it should be possible to develop related catalytic cycles for net diol didehydroxylation that function under milder conditions, comparable to the best current stoichiometric methods. Finally, catalytic cycles utilizing more inexpensive, environmentally friendly reductants, such as hydrogen or carbon monoxide, would facilitate bulk carbohydrate deoxydehydration reactions to produce desirable oxygenated organics. 24 refs., 1 fig.
ISSN 00027863
Educational Use Research
Learning Resource Type Article
Publisher Date 1996-10-02
Publisher Department Brookhaven National Laboratory (BNL), Upton, NY
Publisher Place United States
Journal Journal of the American Chemical Society
Volume Number 118
Issue Number 39
Organization Brookhaven National Laboratory (BNL), Upton, NY


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