THE FORMOIN REACTION

Article abstract of DOI:10.1016/0008-6215(83)88109-9

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.