Journal of the Chemical Society. Perkin transactions I p. 1483 - 1488 (1983)
Update date:2022-08-04
Topics: Conversion Experimental Routes Part 2 Peracid Aromatic ketones
Higgins, Stanley D.
Thomas, C. Barry
Further methods for effecting the oxidative rearrangement of 1-arylalkanones to α-arylalkanoic esters have been investigated.It has been shown that appropriate α-iodoacetals, readily prepared from the ketones, can be converted into esters on treatment either with a peracid or with chlorine.Using the latter reagent, α-chlorination of the ester can be an unwanted side reaction with some substrates and the factors governing by-product formation are discussed.It is demonstrated that, employing chlorine, the process can be made catalytic in iodine.The acetals of 2-amino-1-arylalkanones have also been shown to give high yields of esters under diazotising conditions adding support to the suggestion that the ion, ArC(OR)2CHR', or an incipient version of the ion, is a key intermediate in the process.
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(1983)
