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Paper | Regular issue | Vol 24, No. 9, 1986, pp.2587-2592
Published online, 1st January, 1970
DOI: 10.3987/R-1986-09-2587
Pseudoesters and Derivatives. XXIV. 1,3-Dipolar Cycloaddition of Diazomethane to 5-Methoxyfuran-2(5H)-ones

Francisco Fariña,* M. Victoria Martín, and Férix Sánchez

*Instituto de Química Orgánica General, C. S. I. C., Calle Juan de Cierva, 3, 28006 Madrid, Spain

Abstract

Cycloaddition of diazomethane to 5-methoxyfuran-2(5H)-ones ( 1) occurs in a practically regiospecific manner to give the expected adducts. The cycloadducts are mixtures of the furopyrazoline derivatives 2 and 3 epimeric at C-4, with the exception of those of 1f and 1h that afford only one detectable adduct (2f and 2h) in each case. The regio- and stereochemistry of the adducts follows from the 1H-NMR data. The regiochemistry of the cycloaddition is also corroborated by chemical correlations. Pyrolysis of the epimeric mixtures 2a/3a, 2b/3b and 2d/3d affords the 4-methyl substituted furanones 1c, 1i and 1j in good yields.