Ethers acidic cleavage

Arylalkanoic acid esters, 72 166 Arylaldehydes, microwave-accelerated transformation to nitriles, 76 580-581 Aryl alkyl ethers, acid cleavage of, 70 569 Arylalkylsulfones, 9 273 Arylamine dye intermediates, 9 272t... 

Ether, water, phenylboronic acid. Cleavage occurs by transesterification. 

When it does occur, the Bal2 mechanism is easy to detect, since it is the only one of the base-catalyzed mechanisms that requires inversion at R. However, in the last example given, the mechanism is evident from the nature of the product, since the ether could have been formed in no other way. The Aal2 mechanism has been reported in the acid cleavage of y-lactones. ° ... 

Epoxides are more reactive than other ethers. This is due to ring strain inherent in any three-atom ring system. The most useful reactions are acidic cleavage and nucleophilic cleavage. 

The problem with solvents is that in most cases they decompose under the reaction conditions used in the reductive carbonylation reaction. Solvent decomposition can occur in a variety of ways including (i) acid cleavage of ether linkages by HI and HCo(CO), (ii) well known hydrolysis and halogenation reactions. 

COOH stabilizes the ring towards acid cleavage of the ether bond.)... 

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