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It is used in organic synthesis as an oxidant, often as a solution in acetic acid, [9] or acetone in the case of the Jones oxidation. In these oxidations, the Cr(VI) converts primary alcohols to the corresponding carboxylic acids and secondary alcohols to ketones. The reactions are shown below: Primary alcohols to carboxylic acids
The reaction was an early method for the oxidation of alcohols. Its use has subsided because milder, more selective reagents have been developed, e.g. Collins reagent. [1] The Jones oxidation. Jones reagent is a solution prepared by dissolving chromium trioxide in aqueous sulfuric acid.
Cr(VI)-pyridine and pyridinium reagents have the advantage that they are soluble in organic solvents as are the alcohol substrates. One family of reagents employs the complex CrO 3 (pyridine) 2. [2] Sarett's reagent: a solution of CrO 3 (pyridine) 2 in pyridine. It was popularized for selective oxidation of primary and secondary alcohols to ...
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
Collins reagent is especially useful for oxidations of acid sensitive compounds. Primary and secondary alcohols are oxidized respectively to aldehydes and ketones in yields of 87-98%. [5] Like other oxidations by Cr(VI), the stoichiometry of the oxidations is complex because the metal undergoes 3e reduction and the substrate is oxidized by 2 ...
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The Collins oxidation is an organic reaction for the oxidation of primary alcohols to aldehydes. It is distinguished from other chromium oxide-based oxidations by the use of Collins reagent, a complex of chromium(VI) oxide with pyridine in dichloromethane. [1] [2] Mechanism of the Collins oxidation [3]
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