Hydrodediazoniation of dry arenediazonium o-benzenedisulfonimides with hydrogen peroxide

Synthesis

Volumn , Issue 14, 2004, Pages 2386-2390

  Barbero, Margherita ^a   Degani, Iacopo ^a   Dughera, Stefano ^a   Fochi, Rita ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

Diazonium compounds; Radical reactions; Reductions; Sulfur

Indexed keywords

HYDROGEN PEROXIDE; REACTION KINETICS; STEREOCHEMISTRY;

ELECTRON DONATING EFFECT; ELECTRON WITHDRAWING SUBSTITUENTS; FREE-RADICAL CHAIN MECHANISM;

AMINES;

ARENEDIAZONIUM O BENZENEDISULFONIMIDE DERIVATIVE; DIAZONIUM COMPOUND; HYDROGEN; HYDROGEN PEROXIDE; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; RADICAL REACTION; REACTION TIME; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 5644258443     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831183     Document Type: Article

References (41)

1. (a) Barbero, M.; Degani, I.; Dughera, S.; Fochi, R. Synthesis 2003, 1225; and references cited therein.
2. (b) Barbero, M.; Degani, I.; Fochi, R.; Perracino, P. PCT EP9801145,; Chem. Abstr. 1998, 129, 244942.
3. (c) Barbero, M.; Crisma, M.; Degani, I.; Fochi, R.; Perracino, P. Synthesis 1998, 1171.
4. For a general survey see: (a) Kornblum, N. Org. React. 1944, 262-339; and references cited therein.
5. (b) Wulfman, D. S. In The Chemistry of Functional Groups: The Chemistry of Diazonium and Diazo Groups, Part 1; Patai, S., Ed.; Wiley: New York, 1978, Chap. 8, 286-287; and references cited therein.
6. (c) Zollinger, H. In The Chemistry of Functional Groups: The Chemistry of Triple-Bonded Functional Groups, Part 1; Patai, S.; Rappaport, Z., Eds.; Wiley: New York, 1983, Chap. 15, 642; and references cited therein.
7. (d) Saunders, K. H.; Allen, R. L. M. In Aromatic Diazo Compounds, 3rd ed.; Edward Arnold: London, 1985, Chap. 10, 537-555; and references cited therein.
8. (e) Zollinger, H. Diazo Chemistry I; VCH: Weinheim, 1994, Chap. 10, 222-225; and references cited therein.
9. (f) Zollinger, H. In The Chemistry of Functional Groups: The Chemistry of Amino, Nitroso, Nitro and Related Groups, Suppl. F2, Part 1; Patai, S., Ed.; Wiley: New York, 1996, Chap. 13, 650-651; and references cited therein.
10. (g) A list of reducing agents: Larock, R. C. In Comprehensive Organic Transformations, 2nd ed.; Wiley: New York, 1999, 40-41.
11. (h) Smith, M. B.; March, J. In March's Advanced Organic Chemistry, 5th ed.; Wiley-Interscience: New York, 2001, Chap. 14, 934-935; and references cited therein.
12. Griess, P. Phil. Trans. Roy Soc. London, Ser. A 1864, 683.
13. Typical examples are: (a) Bigelow, L. A.; Johnson, J. R.; Sandborn, L. T. Organic Syntheses Coll. Vol. I; Wiley: New York, 1941, 133-134.
14. (b) Wallingford, V. H.; Krueger, P. A. Organic Syntheses Coll. Vol. II; Wiley: New York, 1943, 353-355.
15. (c) Coleman, G. H.; Talbot, W. F. Organic Syntheses Coll. Vol. II; Wiley: New York, 1943, 592-593.
16. (a) Kornblum, N.; Iffland Don, C. J. Am. Chem. Soc. 1949, 77, 2137.
17. (b) Kornblum, N.; Cooper, G. D.; Taylor, J. E. J. Am. Chem. Soc. 1950, 72, 3013.
18. (c) Kornblum, N.; Kelley, A. E.; Cooper, G. D.; Taylor, J. E. J. Am. Chem. Soc. 1952, 74, 3074.
19. (d) Kornblum, N. Organic Syntheses Coll. Vol. III; Wiley: New York, 1953, 295-299.
20. (a) Hendrickson, J. B. J. Am. Chem. Soc. 1961, 83, 1251.
21. (b) Bloch, M.; Musso, H.; Zahorszky, U. I. Angew. Chem. 1969, 81, 370.
22. (c) Nakayama, J.; Yoshida, M.; Simamura, O. Tetrahedron 1970, 26, 4609.
23. Shono, T.; Matsumura, Y.; Tsubata, K. Chem. Lett. 1979, 1051.
24. Park, K. H.; Cho, Y. H.; Jang, E. J. Bull. Korean. Chem. Soc. 1996, 17, 179.
25. Rutherford, K. G.; Redmond, W. A. J. Org. Chem. 1963, 28, 568.
26. Lormann, M.; Dahmen, S.; Brase, S. Tetrahedron Lett. 2000, 47, 3813.
27. Geoffroy, O. J.; Morinelli, T. A.; Meier, G. P. Tetrahedron Lett. 2001, 42, 5367.
28. (a) Cadogan, J. I. G.; Molina, G. A. J. Chem. Soc., Perkin Trans. 1 1973, 541.
29. (b) Itoh, T.; Matsuya, Y.; Nagata, K.; Ohsawa, A. Tetrahedron Lett. 1996, 37, 4165.
30. (c) Li, F.; Yang, S. I.; Ciringh, Y.; Seth, J.; Martin, C. H.; Singh, D. L.; Kim, D.; Birge, R. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Am. Chem. Soc. 1998, 120, 10001.
31. (a) Doyle, M. P.; Dellaria, J. F.; Siegfried, B.; Bishop, S. W. J. Org. Chem. 1977, 42, 3494.
32. (b) Wassmund, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 1713.
33. Threadgill, M. D.; Gledhill, A. P. J. Chem. Soc., Perkin Trans. 1 1986, 873.
34. Newman, M. S.; Hung, W. M. J. Org. Chem. 1974, 39, 1317.
35. Dictionary of Organic Compounds on CD-ROM, Version 10.2 [CD-ROM]; Chapman & Hall, Electronic Publishing Division: London, 2003.
36. Bulman Page, P. C.; Klair, S. S.; Brown, M. P.; Smith, C. S.; Maginn, S. J.; Mulley, S. Tetrahedron 1992, 48, 5933.
37. Bunnet, J. F. Acc. Chem. Res. 1978, 11, 413.
38. Wassmund, F. W.; Kiesman, W. F. J. Org. Chem. 1997, 62, 8304.
39. (a) Barbero, M.; Degani, I.; Dughera, S.; Fochi, R.; Perracino, P. Synthesis 1999, 90.
40. (b) Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R.; Migliaccio, M. J. Org. Chem. 2000, 65, 5600.
41. (c) Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R. Synthesis 2001, 2180.