Nitronium Acetate Adducts of Furan Derivatives

Article abstract of DOI:10.1021/jo00370a012

An improved procedure for the isolation of the main addition products of the reaction between nitronium acetate and furfural diacetate or methyl 2-furoate is described.The kinetics of the deacetylation of the diastereomeric 1,4-adducts in buffer solutions revealed a substantial primary hydrogen isotope effect.Mild acid-induced alcoholysis transformed the adducts into 2,5-dialkoxy-2,5-dihydrofurans.The reaction chemistry of the furan adducts is compared with the solvolytic pathways reported for ipso nitronium acetate adducts formed from alkylbenzenes.