Conformational analysis and chromic acid oxidation. The rationalization of the rates of oxidation of secondary alcohols

1976 ◽  
Vol 98 (26) ◽  
pp. 8407-8413 ◽  
Author(s):  
Paul Mueller ◽  
Jean C. Perlberger
Keyword(s):  
Conformational Analysis ◽  
Chromic Acid ◽  
Acid Oxidation ◽  
Secondary Alcohols ◽  
Chromic Acid Oxidation

Chromic acid oxidation of aromatic alcohols

1969 ◽  
Vol 47 (17) ◽  
pp. 3207-3212 ◽  
Author(s):  
Ross Stewart ◽  
Fariza Banoo
Keyword(s):  
Chromic Acid ◽  
Acid Oxidation ◽  
Secondary Alcohols ◽  
Tertiary Alcohols ◽  
Chromic Acid Oxidation ◽  
Hydride Shift ◽  
Rate Of Reaction ◽  
Aromatic Alcohols ◽  
Reaction Constant ◽  
Rate Controlling Step

The mechanism of the chromic acid oxidation of di- and tri-aryl carbinols has been studied in 80 wt% acetic acid containing sulfuric acid. The reactions are cleanly second-order and give benzophenones in the case of the secondary alcohols and benzophenones plus phenols in the case of the tertiary alcohols. Electron-donating substituents in the tertiary alcohol appear predominantly in the phenol component and the rate-controlling step is believed to be a 1,2-aryl shift. The reaction constant for the migration is ρ+ = −1.44 and that for the overall reaction is ρ+ = −0.879. The presence of manganous ions does not alter these values although it lowers the overall rate of reaction. Although an analogous 1,2-hydride shift mechanism can be written for the oxidation of the secondary alcohols, there are enough points of difference between the oxidations of the secondary and tertiary systems to make this appear unlikely.

Aqueous chromic acid oxidation of secondary alcohols in diethyl ether: A convenient undergraduate organic chemistry experiment

1979 ◽  
Vol 56 (3) ◽  
pp. 203 ◽  
Author(s):  
Kerry L. Thompson ◽  
S. Krishnamurthy ◽  
Thomas Nylund ◽  
M. Ravindranathan
Keyword(s):  
Organic Chemistry ◽  
Diethyl Ether ◽  
Chromic Acid ◽  
Acid Oxidation ◽  
Secondary Alcohols ◽  
Chromic Acid Oxidation ◽  
Chemistry Experiment

Kinetic Isotope Effect in the Chromic Acid Oxidation of Secondary Alcohols

2000 ◽  
Vol 77 (8) ◽  
pp. 1042 ◽  
Author(s):  
Charles E. Harding ◽  
Christopher W. Mitchell ◽  
Jozsef Devenyi
Keyword(s):  
Isotope Effect ◽  
Kinetic Isotope Effect ◽  
Chromic Acid ◽  
Acid Oxidation ◽  
Secondary Alcohols ◽  
Chromic Acid Oxidation ◽  
Kinetic Isotope

Direct Observation of Intermediates in the Chromic Acid Oxidation of Secondary Alcohols

1967 ◽  
Vol 89 (2) ◽  
pp. 455-457 ◽  
Author(s):  
Kenneth B. Wiberg ◽  
Hans. Schafer
Keyword(s):  
Direct Observation ◽  
Chromic Acid ◽  
Acid Oxidation ◽  
Secondary Alcohols ◽  
Chromic Acid Oxidation

Conformational Analysis. XI. Configurational Equilibria and Chromic Acid Oxidation Rates of Alkylcyclohexanols. Deformation Effects1

1966 ◽  
Vol 88 (14) ◽  
pp. 3327-3334 ◽  
Author(s):  
Ernest L. Eliel ◽  
Siegfried H. Schroeter ◽  
Thomas J. Brett ◽  
Francis J. Biros ◽  
Jean-Claude Richer
Keyword(s):  
Conformational Analysis ◽  
Chromic Acid ◽  
Acid Oxidation ◽  
Oxidation Rates ◽  
Chromic Acid Oxidation
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