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In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids (R−C(=O)OH). A specific example of an acyl chloride is acetyl chloride, CH 3 COCl.
The acid chloride suffers attack by diazomethane with loss of HCl. The alpha-diazoketone (RC(O)CHN 2) product undergoes the metal-catalyzed Wolff rearrangement to form a ketene, which hydrates to the acid. [16] [17] [4] The rearrangement leaves untouched the stereochemistry at the carbon alpha to the acid chloride. [6]
However, for certain reactive acyl chlorides the activity must be reduced further, by the addition of a poison. Originally this was thioquinanthrene although thiourea [ 2 ] has also been used. [ 3 ] [ 4 ] Deactivation is required because the system must reduce the acyl chloride but not the subsequent aldehyde.
Strictly speaking, this reaction results in the formation of a rhodium carbonyl complex rather than free carbon monoxide. The catalytic cycle is assumed to involve oxidative addition of the aldehyde (or acid chloride) to gives a 16e acyl Rh(III)-hydride intermediate, which undergoes migratory extrusion of CO proceed to form an 18-electron d6 Rh ...
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Reaction with carboxylic acids to form mixed anhydrides: ROC(O)Cl + HO 2 CR' → ROC(O)−OC(O)R' + HCl. Typically these reactions would be conducted in the presence of a base which serves to absorb the HCl. Alkyl chloroformate esters degrate to give the alkyl chloride, with retention of configuration: ROC(O)Cl ' → RCl + CO 2