The conversion of d-glucono-1,5-lactone into an α-pyrone derivative |
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Authors: | Charles R Nelson Josef S Gratzl |
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Institution: | Department of Wood and Paper Science, School of Forest Resources, North Carolina State University, Raleigh, N.C. 27607, U.S.A. |
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Abstract: | Treatment of d-glucono-1,5-lactone (3) with excess of acetic anhydride in anhydrous pyridine at room temperature afforded the tetra-acetate and 2,4,6-tri-O-acetyl-3-deoxy-d-erythro-hex-2-enono-1,5-lactone (1). On prolonged reaction or at 80°, 3-acetoxy-6-acetoxymethylpyran-2-one (5) was the unexpected main product. The mechanistic implications of the conversion of 1 → 5 are discussed. |
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