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In a standard amine alkylation reaction, even if the electrophile is the limiting reagent, the equilibrium between the protonated product and the starting amine is rapid enough to result in a complex mixture
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In a standard amine alkylation reaction, even if the electrophile is the limiting reagent, the equilibrium between the protonated product and the starting amine is rapid enough to result in a complex mixture.
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26
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67849089686
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The reaction is conducted by adding 1 equiv of sequestrating agent and 3 equiv of methyl iodide to a solution of n-butylamine (0.035 M) in chloroform at room temperature.
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The reaction is conducted by adding 1 equiv of sequestrating agent and 3 equiv of methyl iodide to a solution of n-butylamine (0.035 M) in chloroform at room temperature.
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31
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53849133462
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For an alternative, catalytic monoarylation protocol see
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For an alternative, catalytic monoarylation protocol see: Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 1355213554.
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35
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67849087824
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In the case of cyclohexylamine, total conversion to the corresponding ammonium salt was incomplete after 16 h at room temperature, indicating the influence of steric effects on the reaction rate
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In the case of cyclohexylamine, total conversion to the corresponding ammonium salt was incomplete after 16 h at room temperature, indicating the influence of steric effects on the reaction rate.
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36
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33846353513
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