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A chromate ester is a chemical structure that contains a chromium atom (symbol Cr) in a +6 oxidation state that is connected via an oxygen (O) linkage to a carbon (C) atom. The Cr itself is in its chromate form, with several oxygens attached, and the Cr–O–C attachment makes this chemical group structurally similar to other ester functional groups.
The mechanism of this process likely depends on the acidity of the chromium reagent. Acidic reagents such as PCC may cause ionization and recombination of the chromate ester (path A), while the basic reagents (Collins) likely undergo direct allylic transposition via sigmatropic rearrangement (path B).
Like conventional esters, the formation of this chromate ester is accelerated by the acid. These esters can be isolated when the alcohol is tertiary because these lack the α hydrogen that would be lost to form the carbonyl. For example, using tert-butyl alcohol, one can isolate tert-butyl chromate ((CH 3) 3 CO) 2 CrO 2), which is itself a good ...
Babler oxidation mechanism. The reaction proceeds through the formation of a chromate ester (1) from nucleophilic attack of the chlorochromate by the allylic alcohol.The ester then undergoes a [3,3]-sigmatropic shift to create the isomeric chromate ester (2).
It can be prepared by treating chromium metal with fluorine at 400 °C and 200 bar pressure. The peroxochromate(V) is another example of the +5 oxidation state. Potassium peroxochromate (K 3 [Cr(O 2) 4]) is made by reacting potassium chromate with hydrogen peroxide at low temperatures. This red brown compound is stable at room temperature but ...
Pyridinium chlorochromate in a vial. Pyridinium chlorochromate (PCC) is a yellow-orange salt with the formula [C 5 H 5 NH] + [CrO 3 Cl] −.It is a reagent in organic synthesis used primarily for oxidation of alcohols to form carbonyls.
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The chromate and dichromate ions are fairly strong oxidizing agents. Commonly three electrons are added to a chromium atom, reducing it to oxidation state +3. In acid solution the aquated Cr 3+ ion is produced. Cr 2 O 2− 7 + 14 H + + 6 e − → 2 Cr 3+ + 7 H 2 O ε 0 = 1.33 V