Abstract
Arylalkynols were converted into both conjugated enynes and arylacetylenic compounds using p-TsCl/Al2O3 and KOH/Al2O3 respectively in classical heating or microwave irradiation methods in good yields.
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36.The physical and/or spectral data of arylalkynols 1A-10A. 1A: m.p. = 54–55°C (lit. m.p. = 51°C). 2A: m.p. = 50.5–51.5°C; IR (KBr, cm–1), 3300, 2985, 2930, 1515, 1369, 1285, 1169, 969, 823; 1H NMR (CDCl3, 500 MHz), δ(ppm) 1.64 (s, 6H), 1.87 (brs, 1H), 2.37 (s, 3H), 7.13 (d, 2H, J = 7.9 Hz), 7.33 (d, 2H, J = 7.9 Hz); 13C NMR (CDCl3, 125 MHz), δ(ppm) 21.85, 31.95, 66.03, 82.64, 93.56, 120.88, 129.41, 131.95, 138.70; MS m/e 174, 159, 141, 131, 115, 91; Anal. calcd for C12H14O: C, 82.76; H, 8.05, found: C, 82.66; H, 8.24%. 3A: m.p. = 56.5–57-5°C (lit. m.p. = 56–57°C). [4A (Table 1) and 5A (Table 2)]: m.p. = 52–53°C. [4A (Table 2)]: m.p. = 115.5–116.5°C; IR (KBr, cm-1), 3331, 2985, 1485, 1369, 1154, 969, 846, 769; 1H NMR (CDCl3, 500 MHz), δ(ppm) 1.69 (s, 6H), 2.30 (s, 1H), 7.38–7.62 (m, 9H); 13C NMR (CDCl3, 125 MHz), δ(ppm) 31.94, 66.11, 82.44, 94.82, 122.04, 127.35, 127.43, 129.27, 132.48, 140.73, 141.39; MS m/e 236, 221, 202, 178, 165, 152; Anal. calcd for C17H16O: C, 86.44; H, 6.78, found: C, 86.70; H, 6.90%. [5A (Table 1) and 7A (Table 2)]: colourless oil (lit. colourless oil). 6A: m.p. = 107.5–108.5°C (lit. colourless oil). [7A (Table 1)]: m.p. = 84.5–85°C (lit. m.p. = 84–85°C). 8A: m.p. = 68.5–69.5°C; IR (KBr, cm-1), 3423, 2977, 2231, 1608, 1500, 1369, 1269, 1108, 969, 808; 1H NMR (CDCl3, 500 MHz), δ(ppm) 1.61 (s, 6H), 2.83 (s, 1H), 7.45 (d, 2H, J = 8.4 Hz), 7.55 (d, 2H, J = 8.4 Hz); 13C NMR (CDCl3, 125MHz), δ(ppm) 31.65, 65.90, 80.90, 98.89, 111.82, 118.83, 128.25, 132.33, 132.53; MS m/e 185, 184, 170, 154, 142, 127, 115; Anal. calcd for C12H11NO: C, 77.84; H, 5.95; N, 7.57, found: C, 77.50; H, 6.15%; N, 7.35. 9A: m.p. = 165–166°C (lit. m.p. = 162–163°C). 10A: m.p. = 177–178°C; IR (KBr, cm–1), 3262, 2985, 2931, 1585, 1415, 1245, 1162, 962, 900, 654. 1H NMR (DMSO-d6, 500 MHz), δ(ppm) 1.47 (s, 18H), 5.45 (s, 3H), 7.33 (s, 3H); 13C NMR (DMSO-d6, 125 MHz), δ(ppm) 32.28, 64.47, 79.45, 98.50, 124.63, 133.96; MS m/e 324, 309, 291, 266, 251, 233, 189, 138; Anal. calcd for C21H24O3: C, 77.78; H, 7.41, found: C, 77.62; H, 7.46%.
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