Conversion of aromatic ketones into α-arylalkanoic acids. Part 2. Routes employing peracid, chlorine, or nitrous acid

Autor:	Stanley D. Higgins, C. Barry Thomas
Rok vydání:	1983
Předmět:	Nitrous acid chemistry.chemical_compound chemistry Reagent Aromatic ketones polycyclic compounds Side reaction Chlorine chemistry.chemical_element Organic chemistry Iodine Ion Catalysis
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :1483-1488
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19830001483
Popis:	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.
Databáze:	OpenAIRE
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