By Gerard V. Smith
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Additional info for Catalysis in Organic Syntheses 1977
Addition/ C H 2^ 0" Η H * * addition / \S Η 0 E / // \f h \ Λ -- CH. 2^ oh < ® - \ * y - C H 2 -CH2 - C ^ 1,2 and 1,4 addition to an a,&-unsaturated The problem with understanding the mechanism of the hydrogenation of a,ß-unsaturated aldehydes is the conflicting reports about the major products and the reaction pathways. What causes the reaction to proceed in different manners? Is there a surface specie(s) which accounts for the conflict ing information on this reaction? Therefore, this study was undertaken to examine the reaction pathways by careful gas chromatographic techniques and deuterium labelling/mass spectrometry.
Instead of hydrocinnamaldehyde, they obtained a mixture of phenylpropane, 3-phenyl-l-propanol and cinnamaldehyde. To further complicate the issue, Bogert and Powell (2) obtained results agreeing with those of Skita. To clarify the situation, Rylander (13) performed a study of factors which affect the products obtained at spontaneous termination of the reaction. It was found that the products obtained were dependent on the method of catalyst preparation, the solvent, the catalyst support, the catalyst, and on any additives.
The metals that have been successfully bound to the resins in this manner are titanium, zirconium, hafmium, niobium, molybdenum and tungsten. The effectiveness of the polymer supported zirconocene trichloride, after reduction with butyl lithium, has been tested. While there is some activity in hydrogenation of some olefins (1 -hexene and cyclohexene) it is not nearly so great as was observed with the corresponding titanium system. The hafnium based analog was about as effective as the zirconium.