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For a related Hg(II)-induced carbocyclization, see: Boaventura, M. A.; Drouin, J. Synth. Commun. 1987, 17, 975.
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58149187082
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We assume that initially formed 2a isomerizes directly into the more stable conjugated compound 3a in the presence of HN(i-Pr) 2 at 70 °C
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2 at 70 °C.
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37
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58149200142
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1H NMR analysis of the crude reaction mixtures.
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1H NMR analysis of the crude reaction mixtures.
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38
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58149182847
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General Procedure. Synthesis of 2h (Table 2, entry 7, A solution of 1h (100 mg, 0.42 mmol) and (c-C6H 11)(i-Pr)NH (20 mol, 12 mg) in CDC13 (0.4 mL) was added to, Ph3PAu)3O]BF4 (7.5 mol, 45 mg, and the reaction vial was sealed, protected from light, and stirred at 70 °C for 18 h (until 1H NMR analysis of the reaction mixture indicated complete conversion, The mixture was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (pentanes/EtOAc, 95/5) gave 2h as a colorless oil (71 mg, 0.30 mmol, 71, R f0.48 (pentanes/EtOAc, 90/10, 1H NMR (360 MHz, CDC13) δ 1.26 (s, 3H, 2.23 (d, J, 14.0 Hz, 1 H, 2.92-3.07 (m, 3 H, 3.73 (s, 3 H, 3.74 (s, 3 H, 4.95 (app. t, J, 2.2 Hz, 1 H, 5.22 (app. t, J, 1.9 Hz, 1 H, 9.29 (s, 1 H, 13C NMR 90.6 MHz, CDC
-
3O)].
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40
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58149179152
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This ring system has not been previously described in the literature
-
This ring system has not been previously described in the literature.
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41
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Ito, Y.; Inouye, M.; Suginome, M.; Muratami, M. J. Organomet. Chem. 1988, 342, C41.
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Muratami, M.4
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