804553-25-1Relevant articles and documents
Thiazol-2-ylidene catalysis in intramolecular crossed aldehyde-ketone benzoin reactions
Enders, Dieter,Niemeier, Oliver
, p. 2111 - 2114 (2004)
Intramolecular crossed aldehyde-ketone benzoin-type reactions catalyzed by nucleophilic carbenes, easily generated from commercially available thiazolium salts as precatalysts, are described. Five- and six-membered cyclic acyloins are obtained in moderate to good yields. Depending on the structure of the aldehyde-ketone substrate, an interchange of the alcohol and ketone function of the resulting acyloin is possible. Simple aldehyde-ketones are not good substrates due to the competing intermolecular reaction. Starting from biphenyl-2,2′-dicarbaldehyde, the intermediate acyloin is converted to 9,10-phenanthrenequinone by mild air oxidation.