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Report | Regular issue | Vol 20, No. 9, 1983, pp.1761-1767
Published online, 1st January, 1970
DOI: 10.3987/R-1983-09-1761
■ Pseudoesters and Derivatives. XVIII. The Reaction of 5-Methoxyfuran-2(5H)-one and Its 3-Halo Derivatives with Nitrogen and Sulphur Nucleophiles

Francisco Fariña, M. Victoria Martín, Félix Sánchez, M. Carmen Maestro, and M. Rosario Martín

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

Abstract

The 5-methoxyfuran-2(5H)-ones 1 - 3 react with amines and thiols under basic catalysis at room temperature in tetrahydrofuran or carbon tetrachloride yielding the corresponding products of conjugate addition. The nucleophile enters preferentially from the side opposite to the OMe group.