Reaction of enamines and mediated anodic oxidation of carbohydrates with the 2,2,6,6-tetramethylpiperidine-1-oxoammonium ion (TEMPO+)

Electrochimica Acta

Volumn 50, Issue 25-26 SPEC. ISS., 2005, Pages 4956-4972

  Schamann M ^a   Schafer H J ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Enaminoester; Imidazolium cation; Maltose; Raffinose; TEMPO +; Uronic acid

Indexed keywords

ANODIC OXIDATION; ESTERS; IONS; MALTOSE; POLYSACCHARIDES; REACTION KINETICS;

ENAMINOESTER; IMIDAZOLIUM CATION; RAFFINOSE; URONIC ACID;

CARBOHYDRATES;

EID: 24344447249     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2005.02.077     Document Type: Conference Paper

References (74)

1. H. Lund O. Hammerich Organic Electrochemistry 4th ed. 2001 Marcel Dekker New York
2. A.J. Bard M. Stratmann Encyclopedia of Electrochemistry H.J. Schäfer Organic Electrochemistry vol. 8 2004 Wiley-VCH Weinheim
3. S. Torii A.J. Bard M. Stratmann Encyclopedia of Electrochemistry H.J. Schäfer Organic Electrochemistry vol. 8 2004 Wiley-VCH Weinheim Chapter 15
4. E. Steckhan Top. Curr. Chem. 42 1987 1
5. S. Torii A.J. Bard M. Stratmann Encyclopedia of Electrochemistry H.J. Schäfer Organic Electrochemistry vol. 8 2004 Wiley-VCH Weinheim Chapter 15, p. 505
6. Y. Kashiwagi, F. Kurashima, S. Chiba, J. Anzai, T. Osa, and J.M. Bobbitt Chem. Commun. 2003 114
7. T. Inokuchi, S. Matsumoto, and S. Torii J. Org. Chem. 56 1991 2416
8. M.F. Semmelhack, C.S. Chou, and D.A. Cortes J. Am. Chem. Soc. 105 1983 4492
9. K. Schnatbaum, and H.J. Schäfer Synthesis 1999 864
10. E.M. Belgsir, and H.J. Schäfer Electrochem. Commun. 3 2001 32
11. M. Schämann, and H.J. Schäfer Eur. J. Org. Chem. 2003 351
12. Y. Kashiwagi, H. Ono, and T. Osa Chem. Lett. 1993 81
13. A.E.J. de Nooy, A.C. Besemer, and H. van Bekkum Synthesis 1996 1153
14. W. Adam, C.R. Saha-Möller, and P.A. Ganeshpure Chem. Rev. 101 2001 3499
15. A. Dijksma, I.W.C.E. Arends, and R.A. Sheldon Platinum Met. Rev. 45 2001 15
16. K. Yasuda, and S.V. Ley J. Chem. Soc., Perkin Trans. 1 2002 1024
17. S. Weik, G. Nicholson, G. Jung, and J. Rademann Angew. Chem. 40 2001 1436
18. S.D. Rychnovsky, T.L. McLernon, and H. Rajapakse J. Org. Chem. 61 1996 1194
19. M.R. Leanna, T. Sowin, and H.E. Morton Tetrahedron Lett. 1992 5029
20. N. Merbouh, J.M. Bobbitt, and Ch. Brueckner J. Carbohydr. Chem. 21 2002 65
21. M.F. Semmelhack, and C.R. Schmid J. Am. Chem. Soc. 105 1983 6732
22. D.H. Hunter, D.H.R. Barton, and W.J. Motherwell Tetrahedron Lett. 1984 603
23. F. MacCorquodale, J.A. Crayston, J.C. Walton, and D.J. Worsfold Tetrahedron Lett. 1990 771
24. J.M. Bobbitt, and Z. Ma Heterocycles 33 1992 641
25. D.H. Hunter, J.S. Racok, A.W. Rey, and Y.Z. Ponce J. Org. Chem. 53 1988 1278
26. R. Siedlecka, and J. Skarzewski Synthesis 1994 401
27. T. Inokuchi, K. Nakagawa, and S. Torii Tetrahedron Lett. 36 1995 3223
28. H. Tanaka, J. Chou, M. Mine, and M. Kuroboshi Bull. Chem. Soc. Jpn. 77 2004 1745
29. N. Merbouh, J.M. Bobbitt, and Ch. Brueckner Org. Prep. Proced. Int. 36 2004 3
30. N. Merbouh, J.M. Bobbitt, and Ch. Brueckner J. Org. Chem. 69 2004 5116
31. N. Merbouh, J.M. Bobbitt, and Ch. Brueckner Tetrahedron Lett. 2001 8793
32. T. Takata, Y. Tsujino, S. Nakanishi, K. Nakamura, E. Yoshida, and T. Endo Chem. Lett. 1999 937
33. J.M. Bobbitt, and Z. Ma Heterocycles 33 1992 641
34. In the technical synthesis acetone and ammonia are condensed to triacetonamine. Catalytic hydrogentation and oxidation of the amino group with hydrogen peroxide affords TEMPO [W. Büschken, M. Kaufhold, P. Bückert (Hüls AG) EP 0574666 (1993);
35. Chem. Abstr. 120 (1995) 270120]. 4-Acetamido-TEMPO is obtained by way of reductive amination of triacetonamine and acetylation of the primary amino group. 4-Hydroxy-TEMPO is prepared by way of sodium borohydride reduction of triacetonamine
36. S.D. Rychnovsky, R. Vaidyanathan, T. Beauchamp, R. Lin, and P.J. Farmer J. Org. Chem. 64 1999 6745
37. K. Chabita, and P.C. Mandal Indian J. Chem., Sect. A: Inorg. Bioinorg. Phys. Theor. Anal. Chem. 41 2002 2231
38. S. Kishioka, T. Ohsaka, and K. Tokuda Electrochim. Acta 48 2003 1589
39. Y. Kashiwagi, T. Nishimura, and J. Anzai Electrochim. Acta 47 2002 1317
40. Y. Kato, Y. Shimizu, L. Yijing, K. Unoura, H. Utsumi, and T. Ogata Electrochim. Acta 40 1995 2799
41. P. Krzyczmonik, and H. Scholl J. Electroanal. Chem. 335 1992 233
42. D. Serve Electrochim. Acta 20 1975 469
43. W. Suemmermann, and U. Deffner Tetrahedron 31 1975 593
44. K.H. Chung, K.Y. Cho, Y. Asami, N. Takahashi, and S. Yoshiba Heterocycles 32 1991 99
45. S.I. Yakimovich, V.A. Khrustalev, and T.A. Favorskaya J. Org. Chem. USSR (Engl. Transl.) 9 1973 1411
46. M.E.F. Braibante, H.S. Braibante, L. Missio, and A. Andricopulo Synthesis 1994 898
47. D. Koch, and H.J. Schäfer Angew. Chem. 12 1973 841
48. T. Ren, Y.-Ch. Liu, and Q.-X. Guo Bull. Chem. Soc. Jpn. 69 1996 2935
49. V.A. Golubev, R.V. Miklyush, Z.G. Rozantsev, Izvest. Akadem. Nauk SSR, Ser. Khim. (1972) 656;
50. Chem. Abstr. 77 (1972) 101344.
51. p = 0.337 mA (0.330 mA)
52. p = 0.269 mA (320 mA)
53. J.M. Bobbitt, M.C. Flores, M. Zhenkum, and T. Huitong Heterocycles 30 1990 1131
54. A. Al Mourabit, M. Beckmann, C. Poupat, A. Ahond, and P. Potier Tetrahedron: Asymm. 12 1996 3455
55. J.-P. Gouesnard, and J. Dorie Bull. Soc. Chim. Fr. 2 1986 253
56. Using the numbering in 10a (Scheme 6) a C,H-correlation is found for: C-13 to C-4 and C-14; C-12 to C-13 and C-5; C-5 to C-12 and C-18; C-18 to C-2; C-17 to C-2 and C-4; C-19 to C-6 and C-2; NH to C-2 and C-7; C-8 to C-9 and C-6; NOE-enhancement between: NH and H at C-8 (E-configuration); H at C-5 and H at C-18; H at C-12 and H at C-17
57. M. Schämann, and H.J. Schäfer Synlett 2004 1601
58. R. Braslau, L.C. Burill II, M. Siano, N. Naik, R.K. Howden, and L.K. Mahal Macromolecules 30 1997 6445
59. C.J. Hawker, W.A. Bosmann, and E. Harth Chem. Rev. 101 2001 3661
60. Ch. Wetter, J. Gierlich, Ch.A. Knoop, Ch. Mueller, T. Schulte, and A. Studer Chemistry 10 2004 1156
61. Ch.A. Knoop, and A. Studer J. Am. Chem. Soc. 125 2003 16327
62. Ch. Wetter, K. Jantos, K. Woithe, and A. Studer Org. Lett. 5 2003 2899
63. H. van Bekkum F.W. Lichtenthaler Carbohydrates as Organic Raw Materials 1991 VCH Verlagsgesellschaft Weinheim 289
64. H. Röper F.W. Lichtenthaler Carbohydrates as Organic Raw Materials 1991 VCH Verlagsgesellschaft Weinheim 267
65. A. Abbadi, and H. van Bekkum Carbohydrates as Organic Raw Materials III 1996 VCH Verlagsgesellschaft Weinheim p. 37
66. T. Mallat, and A. Baiker Catal. Today 19 1994 247
67. K. Heyns, H. Paulsen, G. Rüdiger, and J. Weyer Fortschr. Chem. Forsch. 11 1969 285
68. D.F. Hinkley, A.M. Hoinowski, DE 1813757 (1967);
69. Chem. Abstr. 72 (1970) 32177r.
70. Refs. [11-30] in [4c]
71. Experiments done by T. Breton, University of Poitiers, France, during a stay in Münster
72. A.E. de Nooy, A.C. Besemer, H. van Bekkum, J.A.A.P. van Dijk, and J.A.M. Smit Macromolecules 29 1996 6541
73. I. Shibata, and A. Isogai Cellulose 10 2003 335
74. J.-F. Thaburet, N. Merbouh, M. Ibert, F. Marsais, and G. Queguiner Carbohydr. Res. 330 2001 21