Journal of Organic Chemistry p. 3811 - 3818 (1986)
Update date:2022-09-26
Topics:
Balina, Gisela
Kesler, Patricia
Petre, Janet
Pham, Dung
Vollmar, Arnulf
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.
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