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Vinazene (2-vinyl-4,5-dicyanoimidazole) was provided by Prof. Paul Rasmussen from the University of Michigan, Department of Chemistry. Samples are available from this source.
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Vinazene (2-vinyl-4,5-dicyanoimidazole) was provided by Prof. Paul Rasmussen from the University of Michigan, Department of Chemistry. Samples are available from this source.
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15
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34247617666
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General procedure for the preparation of the vinazene derivatives. Alkyl Vinazene. To a solution of vinazene (1.00 g, 6.9 mmol) in 15 mL of acetone was added anhydrous K2CO3 (1.40 g, 10.1 mmol) and 1-iodohexane (1.40 mL, 9.5 mmol, The solution was refluxed for 24 h and filtered and the was solvent removed under a vacuum. Water (30 mL) was then added to the oily residue and the aqueous layer was extracted three times with 50 mL aliquots of ethyl acetate. The organic layer was dried over magnesium sulfate and the solvent was removed under a vacuum. The oily residue was recrystallized in EtOH to give pale yellow crystalline solids (1.42 g, 90% yield) after 24 h at 4°C. 1H NMR (CDCl3, δ 0.90 (t, 3 H, J, 6.8 Hz, 1.33 (unresolved m, 6 H, 1.80 (q, 2 H, J, 6.8 Hz, 4.11 (t, 2 H, J, 7.2 Hz, 5.82 (t, 1 H, J, 6.4 Hz, 6.52 (d, 2 H, J, 6.0 Hz, 13C NMR CDCl3, δ 14
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10S, 588.
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Lee, J.W.7
Gal, Y.-S.8
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Kietzke, T.1
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Neher, D.3
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