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Darmenton, P.; Philippe, M. FR 2757383, 1996; Chem. Ahstr. 1998, 129, 140458n.
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34249826725
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For a review on the synthesis of anthocyanidins, see
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36649009448
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A similar approach, using sulfuric acid, has been mentioned in the early fifties and surprisingly reported only once thereafter: (a) Johnson, A. W.; Melhuish, R. R. J. Chem. Soc. 1947, 346.
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A similar approach, using sulfuric acid, has been mentioned in the early fifties and surprisingly reported only once thereafter: (a) Johnson, A. W.; Melhuish, R. R. J. Chem. Soc. 1947, 346.
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31
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34249808006
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Apigeninidin Trimethylether Hexafluorophosphate (10) Purple powder; yield 93, mp 201°C. IR(KBr, 1652, 1640 (s, C=O, 1600, 1569, 1506, 1456, 1436, 1378, 1339, 1241, 1124, 1052, 834 (m, P-F) cm-1. UV/Vis [MeOH-HCl (5, 1 N, λmax (ε, 266 (24900, 394 (18000, 460 nm (13600 M-1·cm-1, 1H NMR [300 MHz, CD3CN-TFA-d1, 1, δ, 3.96 (3 H, s, OCH3, 4.07 (3 H, s, OCH3, 4.09 (3 H, s, OCH 3, 6.80 (1 H, d, J, 2.2 Hz, 7.19 (2 H, m, 7.23 (1 H, dd, J, 2.2, 0.7 Hz, 8.05 (1 H, d, J, 8.5 Hz, 8.32 (2 H, m, 9.07 (1 H, dd, J, 8.5 Hz, 5J, 0.7 Hz, 13C NMR [75 MHz, CD3CN-TFA-d1, 1, δ, 55.9/57.0/57.2 (OCH3, 93.4, 99.8, 111.3, 113.4, 115.8, 120.8, 131.9, 148.7, 158.8, 159.0, 167.0, 171.4, 171.7. MS (ESI, positive mode, 297 100, M
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+]. HRMS (ESI): m/z calcd: 297.1121; found: 297.1109.
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37
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34249806424
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Chrysinidin Hexafluorophosphate (13) Orange powder; yield 91, IR (KBr, 3412 (s, br, OH, 1642 (s, C=O, 1580, 1563, 1541, 1381, 1340, 1269, 1239, 1203, 1193, 835 (m, P-F) cm-1. UV/Vis [MeOH-HCl (5, 1 N, λmax (ε, 274 (35400, 474 nm (36200 M -1·cm-1, 1H NMR [300 MHz, CD 3CN-TFA-d1 (1, δ, 6.81 (1 H, d, J, 2.2 Hz, 7.11 (1 H, dd, J, 2.2, 0.7 Hz, 7.72 (2 H, m, 7.84 (1 H, m, 8.13 (1 H, d, J, 8.4 Hz, 8.35 (2 H, m, 9.25 (1 H, dd, J, 8.4, 0.7 Hz, 13C NMR [75 MHz, CD3CN-TFA-d1, 1, δ, 95.7. 102.9, 111.2, 114.4, 128.9, 129.1, 130.0, 135.8, 150.5, 158.4, 159.4, 171.1, 171.4, MS (ESI, positive mode, 239 (100, M, HRMS ESI, m/z calcd: 239.0703; found: 239.0696
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+]. HRMS (ESI): m/z calcd: 239.0703; found: 239.0696.
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38
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34249819449
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All synthesized compounds exhibit NMR spectroscopic data identical to-previously reported ones in the literature.10-12
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10-12
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