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- W2003856646 abstract "Abstract Although additions of α-pyrones to dienophiles have received extensive study,1 there have been few reports of additions of α-pyrones to quinones.2 In attempts to add benzoquinone (1) to coumalic acid (2), we have found that keeping these compounds in methanol and acetic acid in the presence of sodium acetate for 4 hours at 0°C followed by removal of the solvents under reduced pressure and purification by flash chromatography gave compound 3 3 (22%4) mp 158–161°C raised to mp 160–162°C (benzene) UV (MeOH) λ;306 nm (ε 4700), 215 (12,500); IR (CHCl3) vmax 3340, 1770 cm−1; 1H NMR ((CD3)2CO) δ 3.5 (s, 3H), 5.52 (s, 1H), 6.35 (d, J=5 Hz, 1H), 6.55 (m, 1H), 6.85 (m, 2H), 7.55 (d, J=5 Hz, 1H); 13C 171.5, 153.8, 153.4, 150.9, 122.3, 121.8, 119.6, 111.8, 110.8, 94.7, 56.9; mass specteum m/e (relative intensity) 234.0530 (54), 202.0267 (100), 174.0320 (34), 146.0367 (88), 98.0371 (47); m/e calcd for C12H10O5." @default.
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- W2003856646 date "1981-01-01" @default.
- W2003856646 modified "2023-10-16" @default.
- W2003856646 title "The Reaction of Coumalic Acid with Benzoquinone: Formation of a Spirobutenolide" @default.
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- W2003856646 doi "https://doi.org/10.1080/00397918108065758" @default.
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