Carbohydrate Research p. 197 - 208 (1983)
Update date:2022-08-05
Topics:
Castells, Josep
Lopez-Calahorra, Francisco
Geijo, Fernando
The formoin reaction, i.e., the autocondensation of formaldehyde in an aprotic solvent catalysed by the conjugate base of a thiazolium ion, has been studied in detail.Glucose, galactose, dihyroxyacetone dimer, xylose, and arabinose have been identified as products.The influence of catalysts, temperature, basicity, and reaction time is documented.N,N-Dimethylformamide is a more convenient solvent than ether, benzene, or diglyme.Ethyldi-isopropylamine affords better yields of carbohydrate material than triethylamine.At =<60 deg, aldol condensations are reduced to a minimum.After 1-2 h of reaction (depending on the conditions), the yields begin to decrease and become zero after ca. 24 h.
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