ORGN 167 |
| We report a hydride transfer reaction from isopropanol (IPA) to 9-phenylxanthenium ion (PhXn+) in isopropanol containing water or acetonitrile (AN). The kind hydride transfer reaction last appeared in the literature half a century ago when a number of examples of triphenylmethanol and derivatives (as their cations) abstracting hydride ion from aliphatic alcohols in 50% sulfuric acid aqueous solution were reported. The isopropanol adduct of PhXn+ was isolated from a room temperature reaction in 50%IPA/50%AN and was converted to the hydride transfer product when the reaction temperature was increased. The kinetics of the hydride transfer product formation was determined under various acid concentration conditions. The rate was found to increase with increasing the acid concentration, reach a maximum and then decay. Other factors affecting the rate of the reaction have also been investigated, including isotope labeling, temperature, counter ion and solvent. The hydride transfer reaction most likely involves the adduct in a side equilibrium with the two reactants. |
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Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster
Division of Organic Chemistry |