Nitronium acetate adducts of furan derivatives

…, P Kesler, J Petre, P Dung, A Vollmar

Index: Balina, Gisela; Kesler, Patricia; Petre, Janet; Pham, Dung; Vollmar, Arnulf Journal of Organic Chemistry, 1986 , vol. 51, # 20 p. 3811 - 3818

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Citation Number: 12

Abstract

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, Cadducts 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 ...