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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. A variety of related compounds are known with similar reactivity.
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).
The second family of reagents are salts, featuring the pyridinium cation (C 5 H 5 NH +). pyridinium dichromate (PDC) is the pyridium salt of dichromate, [Cr 2 O 7] 2-. pyridinium chlorochromate (PCC) is the pyridinium salt of [CrO 3 Cl] −. These salts are less reactive, more easily handled, and more selective than Collins reagent in ...
A second family of Cr(VI) reagents are salts, featuring the pyridinium cation (C 5 H 5 NH +). pyridinium dichromate (PDC) is the pyridium salt of dichromate, [Cr 2 O 7] 2-. pyridinium chlorochromate (PCC) is the pyridinium salt of [CrO 3 Cl] −. These salts are less reactive, more easily handled, and more selective than Collins reagent in ...
Collins reagent can be used as an alternative to the Jones reagent and pyridinium chlorochromate (PCC) when oxidizing secondary alcohols to ketones. PCC and pyridinium dichromate (PDC) oxidations have largely supplanted Collins oxidation. [1]
The A ring was functionalized with a hydroxyl group through pyridinium chlorochromate oxidation of α-acylketone 49 to form ketone 50. Subsequent reduction using sodium borohydride produced alcohol 51. Reaction of this alcohol with the Ojima lactam 52 and a concluding silyl deprotection step at two triethyl silyl positions in compound 53 gave ...
The Cornforth reagent (pyridinium dichromate or PDC) is a pyridinium salt of dichromate with the chemical formula [C 5 H 5 NH] 2 [Cr 2 O 7].This compound is named after the Australian-British chemist Sir John Warcup Cornforth (b. 1917) who introduced it in 1962.
In the reaction, the alcohol nucleophilically displaces chlorine from the electropositive chromium(VI) metal. The chloride anion then acts as a base to afford the aldehyde product and chromium(IV). The slightly acidic character of PCC makes it useful for cyclization reactions with alcohols and alkenes (Scheme 2). [13]