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(a) Nakazono, S.; Karasawa, S.; Koga, N.; Iwamura, H. Angew. Chem. Int. Ed. 1998, 37, 1550;
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33646568998
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note
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USD 285.80 for 5 g (ALDRICH 2005-2006).
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15
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Mendicino, M.E.3
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3CN=O is described but no detailed procedure is given: Chiarelli, R.; Rassat, A. Tetrahedron 1973, 29, 3639.
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Chiarelli, R.1
Rassat, A.2
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24
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0003199590
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Wiley: New York
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A laborious 3-step preparation of the product A on a large scale via the hydroxylamine 3a is described: Calder, A.; Forrester, A. R.; Hepburn, S. P. Org. Synth. Coll. Vol. VI; Wiley: New York, 1972, 803.
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Org. Synth. Coll.
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Calder, A.1
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Hepburn, S.P.3
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(c) White, E. H.; Ribi, M.; Cho, L. K.; Egger, N.; Dzadzic, P. M.; Todd, M. J. J. Org. Chem. 1984, 49, 4866.
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3 (2c) is reported: Phanstiel, O.; Wang, Q. X.; Powell, D. H.; Ospina, M. P.; Leeson, B. A. J. Org. Chem. 1999, 64, 803.
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Leeson, B.A.5
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30
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33646560825
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note
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-).
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33
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37049083832
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1H NMR signals of the amide matches with those described in literature, see: Larsen, J.; Jorgensen, K. A.; Christensen, D. J. Chem. Soc., Perkin Trans. 1 1991, 1187.
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J. Chem. Soc., Perkin Trans. 1
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Larsen, J.1
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Christensen, D.3
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34
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33646591131
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note
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2K with the starting tert-butylamine (1a) remaining intact.
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35
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33646543620
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note
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3 was efficient enough to provide a complete conversion of the more hydrophobic amine 1c to the benzoyl derivative 2c. Apparently, a fine balance between hydrophilicity, basicity and aqueous solubility precluded the formation of the respective tert-alkyl-ammonium benzoate under the reaction conditions.
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36
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0013571312
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Dicks, P. F.; Glover, S. A.; Goosen, A.; McCleland, C. W. Tetrahedron 1987, 43, 923.
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Dicks, P.F.1
Glover, S.A.2
Goosen, A.3
McCleland, C.W.4
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37
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33646567992
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note
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Dimerization time and hence the crystallization time dramatically increases with the increase of the steric demands of the tert-alkyl substituent: ca. 20-30 min for A, several hours in the refrigerator (+4 °C) for B, and at least a week in a deep freezer (-18 °C) for C. For the NMR study on the monomer-dimer equilibrium, see ref. 10a.
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note
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NMR monitoring of the blue liquid nitroso monomer C prior to the crystallization showed that it was sufficiently pure to be used as a reactant in subsequent transformations.
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6044276841
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Usuki, T.; Mita, T.; Lear, M. J.; Das, P.; Yoshimura, F.; Inoue, M.; Hirama, M.; Akiyama, K.; Tero-Kubota, S. Angew. Chem. Int. Ed. 2004, 43, 5249;
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Lear, M.J.3
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Yoshimura, F.5
Inoue, M.6
Hirama, M.7
Akiyama, K.8
Tero-Kubota, S.9
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33646559426
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Usuki, T.; Mita, T.; Lear, M. J.; Das, P.; Yoshimura, F.; Inoue, M.; Hirama, M.; Akiyama, K.; Tero-Kubota, S. Angew. Chem. 2004, 116, 5361.
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Hirama, M.7
Akiyama, K.8
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(b) Itoh, T.; Matsuda, K.; Iwamura, H. Angew. Chem. Int. Ed. 1999, 38, 1791;
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Itoh, T.1
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Itoh, T.; Matsuda, K.; Iwamura, H. Angew. Chem. 1999, 111, 1886.
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Itoh, T.1
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The research on new type of metal-free nitrogen bases is currently in progress in our laboratory.
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