A mild oxidation method of hydroxamic acids: efficient trapping of acyl nitroso intermediates
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Publisher
Elsevier BV
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference14 articles.
1. For reviews, see: (a) Kirby, G. W. Chem. Soc. Rev. 1977, 6, 1; (b) Dao, L. H.; Dust, J. M.; Mackay, D.; Watson, K. N. Can. J. Chem. 1979, 57, 1712; (c) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087; (d) Boger, D. L. Tetrahedron 1983, 39, 2869; (e) Boger, D. L.; Weinreb, S. M. Hetero Diels–Alder Methodology in Organic Synthesis; Pergamon Press: San Diego, 1987; (f) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990; (g) Albini, A. Synthesis 1993, 263; (h) Streith, J.; Defoin, A. Synthesis 1994, 1107; (i) Zuman, P.; Shah, B. Chem. Rev. 1994, 94, 1621; (j) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 187, 1; (k) Vogt, P. F.; Miller, M. J. Tetrahedron 1998, 54, 1317.
2. For recent papers on the synthetic applications of nitroso intermediates, see: (a) Danishefsky, S. J.; McClure, K. F. J. Org. Chem. 1991, 56, 850; (b) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 33, 3583; (c) Zuman, P.; Shah, B. Chem. Rev. 1996, 94, 1621; (d) Quadrelli, P.; Gamba, I. A.; Caramella, P. Tetrahedron Lett. 1996, 37, 1909; (e) Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, K. J. Org. Chem. 1998, 63, 8397; (f) Ware, Jr., R. W.; King, S. B. J. Am. Chem. Soc. 1999, 121, 6769; (g) Ware, Jr., R. W.; King, S. B. J. Org. Chem. 2000, 65, 8725; (h) MacAuley, B. J.; Nieuwenhuyzen, M.; Sheldrake, G. N. Org. Lett. 2000, 2, 1457; (i) Sparks, S. M.; Vargas, J. D.; Shea, K. J. Org. Lett. 2000, 2, 1473; (j) Ozawa, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2000, 2, 2955; (k) Nakagawa, H.; Sugahara, T.; Ogasawara, K. Org. Lett. 2000, 2, 3181; (l) Arribas, C.; Carereno, M. C.; Garcia-Ruano, J. L.; Rodoriguez, J. F.; Santos, M.; Sanz-tejedor, M. A. Org. Lett. 2000, 2, 3165; (m) Adam, W.; Bottke, N.; Krebs, O. Org. Lett. 2000, 2, 3293; (n) Surmann, M. D.; Miller, M. Org. Lett. 2001, 3, 519.
3. Ref. 1a.
4. Generation of Acyl Nitroso Compounds by the Oxidation of N-Acyl Hydroxylamines with the Dessmartin Periodinane
5. Synthesis of Aryl Nitroso Derivatives by tert-Butyl Hypochlorite Oxidation in Homogeneous Media. Intermediates for the Preparation of High-Hyperpolarizability Chromophore Skeletons
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