An efficient synthesis of 4-Halo-5-hydroxyfuran-2(5H)-ones via the sequential halolactonization and gamma-hydroxylation of 4-aryl-2,3-alkadienoic acids.

Source:http://linkedlifedata.com/resource/pubmed/id/14961712

J. Org. Chem. 2004 Feb 20 69 4 1429-31

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Authors

Dye I, Ma S, Shi Z

Affiliation

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China. masm@mail.sioc.ac.cn

Abstract

4-Halo-5-hydroxyfuran-2(5H)-ones were synthesized via the efficient sequential halolactonization-hydroxylation reaction of 4-aryl-2,3-allenoic acids with I(2) or CuX(2) (X = Br or Cl) in moderate to good yields. The structures of the products were established by the X-ray single-crystal diffraction study of 3-methyl-4-iodo-5-phenyl-5-hydroxyl-2(5H)-furanone (2a). A rationale for this reaction was discussed based on some brief mechanistic study.

PMID
14961712

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