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Indian Journal of Chemistry -Section A (IJC-A) >
IJC-A Vol.46A [2007] >
IJC-A Vol.46A(03) [March 2007] >
| Title: | Kinetics and mechanism of the oxidation of some ⍺-hydroxy carboxylic acids by [bis(trifluoroacetoxy)iodo]benzene |
| Authors: | Banerji, Jayshree
Sharma, Pradeep K
Banerji, Kalyan K |
| Issue Date: | Mar-2007 |
| Publisher: | CSIR |
| IPC Code: | Int. Cl. ⁸ C07B33/00 |
| Abstract: | The oxidation of ⍺-hydroxy carboxylic acids by [bis(trifluoroacetoxy)iodo]benzene (TFAIB), to the corresponding oxoacids is first order with respect to each, the hydroxy acid, TFAIB and hydrogen ions. The oxidation of ⍺-deuteriomandelic acid (PhCDOHCO₂H) exhibits the presence of a substantial pri-mary isotope effect confirming the cleavage of the ⍺ – C – H bond in the rate-determining step. The rate of oxidation of substi-tuted mandelic acids correlates well with Brown’s ⍺⁺ values with large negative reaction constants. A mechanism involving transfer of a hydride ion from the hydroxy acid to the oxidant has been postulated. |
| Page(s): | 445-448 |
| ISSN: | 0376-4710 |
| Source: | IJC-A Vol.46A(03) [March 2007]
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