Dicarbonyl compounds Baeyer-Villiger reaction

Ketones, Aldehydes, and Alcohols. The well-known Baeyer-Villiger oxidation of ketones by Oxone (eq 2) has been exploited in a variety of reactions. This protocol has been used with KHSO5 for cleavage of a- and /3-dicarbonyl compounds to esters or acids (eqs 30 and 31). This process is sirr5>ler, cheaper, and milder than the commonly used haloform reaction. 

Miscellaneous. Sodium bromide or sodium iodide can be used with Amberlyst 15 to effect regioselective ring-opening reactions of substituted aziridlne-2-carboxylates to a-halo- -amino esters. 1,3 Dicarbonyl compounds can be brominated using potassium bromate/potasslum bromide in the presence of Dowex resin.Amberlyst 15 bound sulfonic acid groups are oxidized by aqueous hydrogen peroxide at 70 °C and the peracid that is formed has been used in Baeyer-Villiger oxidation of cyclopentanone. ... 

Atom insertions constitute another important family of reactions. Insertion of single atoms into carbon-carbon cr-bonds change difunctional relationships from odd to even (or even to odd). Cyclohexanones (for example 121) are preparable from 1,5-dicarbonyls (see Functional Groups-11) or 1,7-dicarbonyls. Baeyer-Villiger and Beckman rearrangments convert cyclohexanones into 1,6-difunctional compounds. Conversely, cyclopentanones (for example 123) can be prepared from 1,4-dicarbonyls or 1,6-dicarbonyls vide supra) and can be similarly converted to 1,5-difunctional compounds. This is also true for acyclic compounds (127 —> 128 and 129 130). Carbon insertion reac-... 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ ]

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