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Chloracylierung und Bromacylierung von Carbonylverbindungen. III . Lage des Gleichgewichts
Author(s) -
Bigler Peter,
Neuenschwander Markus
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610621
Subject(s) - chemistry , cyclobutanone , cyclohexanone , halide , equilibrium constant , medicinal chemistry , lewis acids and bases , organic chemistry , catalysis , ring (chemistry) , inorganic chemistry
Chloroacylation and Bromoacylation of Carbonyl Compounds III. Reactant/Product Equilibria Aliphatic, α, β‐unsaturated and aromatic aldehydes 1 as well as aliphatic ketones react with acyl halides 2 to α‐haloalkyl esters 3 . In the presence of Lewis acids there is an equilibrium between reactants and product. The position of the equilibrium depends on the nature of the carbonyl compound as well as that of the acyl halide: The products 3 are favoured in the case of aldehydes, cyclobutanone and cyclohexanone, and the equilibrium constant increases in the series F < Cl < Br < I. Low reaction temperature, nonpolar solvents as well as high reactant concentrations favour the product 3 .