6922-38-9Relevant academic research and scientific papers
REACTION OF ALKOXYFURAN AND ALKOXYPYRANS WITH ALCOHOLS IN ACID MEDIUM
Likhosherstov, V. M.
, p. 1176 - 1178 (2007/10/02)
The acetals of fumaraldehyde and glutaraldehyde are respectively formed when 2,5-dialkoxy-2,5-dihydrofuran and 2-alkoxy-2,3-dihydropyrans are reacted with alcohols in acid medium.The monomethyl-substituted alkoxypyrans are cleaved to glutaraldehyde acetals with much greater difficulty than the unsubstituted derivatives.A 2-alkoxy-3,3-dimethylpyran and 2,5-dialkoxy-2-methylpyran do not give the corresponding acetals.The stability of the methyl-substituted alkoxypyrans is caused by the fact that the methyl groups shield the oxygen of the pyran ring, thus preventing the addition of a proton to the oxygen of the ring.The reason for the resistance of a 2,5-dialkoxy-2-methylfuran to alcoholysis was not ascertained.A mechanism is given for the opening of alkoxy-2,3-dihydropyrans to glutaraldehyde acetals.
