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Natural Science Forum / Chemistry / Organic Synthesis / January 2004Clemmensen reduction of a,b unsaturated aldehyde
Hello! Can a Clemmensen reduction be used in this example to reduce the aldehyde group to methyl without affecting the double bond? R-CH=CH-CHO -> R-CH=CH-CH3 Thanks  SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Clemmensen reductions are more often used with benzyl compounds. I don't believe that the reaction would take place in appreciable yield since the reaction takes place in a strongly acidic medium; the pi electrons will be vulnerable to electrophilic attack. You might want to look up wolff-kishner reduction. -------------------------------------------------------------------------------- GeneralChemistryHomework http://groups.msn.com/GeneralChemistryHomework http://www.chemicalforums.com http://www.physicsforums.com > Hello! > [quoted text clipped - 4 lines] > > Thanks SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Hi, no, both groups may be reduced, or in some cases, only the double bond is reduced. Ivana. > Hello! > [quoted text clipped - 4 lines] > > Thanks SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Anyone? Any idea? I've been searching the literature, though without any luck... > Hello! > > Can a Clemmensen reduction be used in this example to reduce the aldehyde > group to methyl without affecting the double bond? > R-CH=CH-CHO -> R-CH=CH-CH3 > > Thanks SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA |
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