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Arduengo III A.J., Krafczyk R., Schmutzler R., Craig H.A., Goerlich J.R., Marshall W.J., and Unverzagt M. Tetrahedron 55 (1999) 14523
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38849161554
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For review see:. Kizirian J.-C. Chem. Rev. 108 (2008) 140
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For a review see:
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For a review see:. Müller T.E., Hultzsch K.C., Yus M., Foubelo F., and Tada M. Chem. Rev. 108 (2008) 3795
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74749091661
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note
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Typical experimental procedure for N-monoalkylation of amines in water: 2,4,6-trimethylaniline (8.45 mL, 60 mmol) and 1,2-dibromoethane (6.15 g, 30 mmol) were sequentially added at room temperature to water (15 mL). The two-layered solution was vigorously stirred at 95 °C overnight. The solution was cooled to room temperature and 15 mL of water was added. Extraction with 3 × 15 mL of EtOAc and evaporation of the aqueous phase furnished a brown solid which was recrystallized from MeOH/EtOAc to yield 7.1 g (21 mmol, 70%) of 15a as a white solide.
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63
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74749102007
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note
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Ethanol and isopropanol were also tested but with poor success.
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64
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74749108526
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note
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Procedure for the preparation of (N,N′-dicyclohexyl) 1,2-ethanediamine dihydrobromide 21d in alcoholic solvent: Cyclohexylamine (20.0 g, 202 mmol, 3.0 equiv) and 1,2-dibromoethane (12.6 g, 67.0 mmol, 1.0 equiv) were sequentially added at room temperature to methanol (50 mL). The solution was vigorously stirred under reflux overnight. The solution was evaporated under reduced pressure to furnish a brown solid which was triturated with acetone (40 ml), filtrated, and washed with acetone to yield 16.7 g of compound 21d as a white solid (65%).
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66
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0033598258
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For SIMes,HCl, see Ref. 5For SIAd, HCl, see:
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For SIMes,HCl, see Ref. 5For SIAd, HCl, see:. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
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Scholl, M.1
Ding, S.2
Lee, C.W.3
Grubbs, R.H.4
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67
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44349094826
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For SINap, HCl see:
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For SINap, HCl see:. Luan X., Mariz R., Gatti M., Costabile C., Poater A., Cavallo L., Linden A., and Dorta R. J. Am. Chem. Soc. 130 (2008) 6848-6858
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Luan, X.1
Mariz, R.2
Gatti, M.3
Costabile, C.4
Poater, A.5
Cavallo, L.6
Linden, A.7
Dorta, R.8
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