Alkyl- and arylthiodediazoniations of dry arenediazonium o-benzenedisulfonimides. Efficient and safe modifications of the stadler and ziegler reactions to prepare alkyl aryl and diaryl sulfides

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5600-5608

  Barbero, Margherita ^a   Degani, Iacopo ^a   Diulgheroff, Nicola ^a   Dughera, Stefano ^a   Fochi, Rita ^a   Migliaccio, Mara ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ARENEDIAZONIUM O BENZENEDISULFONIMIDE DERIVATIVE; BENZENE DERIVATIVE; DIAZONIUM COMPOUND; DISULFIDE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; STEREOSPECIFICITY; SYNTHESIS; TEMPERATURE;

EID: 0033832827     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0003347     Document Type: Article

References (52)

1. (a) Barbero, M.; Degani, I.; Fochi, R.; Perracino, P. (National Research Council of Italy) PCT/EP98/01145, 1998; Chem. Abstr. 1998, 129, 244942.
2. (b) Barbero, M.; Crisma, M.; Degani, I.; Fochi, R.; Perracino, P. Synthesis 1998, 1171.
3. (c) Barbero, M.; Degani, I.; Dughera, S.; Fochi, R.; Perracino, P. Synthesis 1998, 1235.
4. (d) Barbero, M.; Degani, I.; Dughera, S.; Fochi, R.; Perracino, P. Synthesis 1999, 90.
5. (e) Barbero, M.; Degani, I.; Dughera, S.; Fochi, R. J. Org. Chem. 1999, 64, 3448.
6. Bart, H. M. German Patent 281,055, 1913; Chem. Abstr. 1915, 9, 1830.
7. Stadler, O. Chem. Ber. 1884, 17, 2075.
8. Ziegler, J. H. Chem. Ber 1890, 23, 2469.
9. Saunders, K. H.; Allen, R. L. M. Aromatic Diazo Compounds, 3rd ed.; Edward Arnold: London, 1985; and references therein.
10. Zollinger, H. Diazo chemistry I; WCH: Weinheim, 1994; and references therein.
11. (a) Saunders, K. H.; Allen, R. L. M. Aromatic Diazo Compounds, 3rd ed.; Edward Arnold: London, 1985; p 722.
12. (b) Yildirir, Y.; Okay, G. Org. Prep. Proced. Int. 1991, 23, 198 and references therein.
13. For example, see: (a) Elbel, E. Henkel & Cie. G.m.b.H., German Patent 614,311, 1935; Chem. Abstr. 1935, 29, 5862. (b) Baleja, J. D. Synth. Commun. 1984, 14, 215. (c) Schaefer, T.; Baleja, J. D. Can. J. Chem. 1986, 64, 1376.
14. For example, see: (a) Elbel, E. Henkel & Cie. G.m.b.H., German Patent 614,311, 1935; Chem. Abstr. 1935, 29, 5862. (b) Baleja, J. D. Synth. Commun. 1984, 14, 215. (c) Schaefer, T.; Baleja, J. D. Can. J. Chem. 1986, 64, 1376.
15. For example, see: (a) Elbel, E. Henkel & Cie. G.m.b.H., German Patent 614,311, 1935; Chem. Abstr. 1935, 29, 5862. (b) Baleja, J. D. Synth. Commun. 1984, 14, 215. (c) Schaefer, T.; Baleja, J. D. Can. J. Chem. 1986, 64, 1376.
16. For example, see: (a) Petrillo, G.; Novi, M.; Garbarino, G.; Dell'Erba, C. Tetrahedron 1986, 42, 4007 and references therein. (b) Abeywickrema, A. N.; Beckwith, A. L. J. J. Am. Chem. Soc. 1986, 108, 8227 and references therein. (c) Permual, S.; Chandrasekaran, R.; Vijayabaskar, V.; Wilson, D. A. Magn. Reson. Chem. 1995, 33, 779 and references therein.
17. For example, see: (a) Petrillo, G.; Novi, M.; Garbarino, G.; Dell'Erba, C. Tetrahedron 1986, 42, 4007 and references therein. (b) Abeywickrema, A. N.; Beckwith, A. L. J. J. Am. Chem. Soc. 1986, 108, 8227 and references therein. (c) Permual, S.; Chandrasekaran, R.; Vijayabaskar, V.; Wilson, D. A. Magn. Reson. Chem. 1995, 33, 779 and references therein.
18. For example, see: (a) Petrillo, G.; Novi, M.; Garbarino, G.; Dell'Erba, C. Tetrahedron 1986, 42, 4007 and references therein. (b) Abeywickrema, A. N.; Beckwith, A. L. J. J. Am. Chem. Soc. 1986, 108, 8227 and references therein. (c) Permual, S.; Chandrasekaran, R.; Vijayabaskar, V.; Wilson, D. A. Magn. Reson. Chem. 1995, 33, 779 and references therein.
19. (a) British Chemical Industry Safety Council Quarterly Safety Summary 1969, 40, 158.
20. (b) Spencer, H. Chem. Br. 1977, 13, 240 and references therein.
21. Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413 and references therein.
22. (a) Bunnett, J. F.; Kim, J. K. J. Am. Chem. Soc. 1970, 92, 7463.
23. (b) Bunnett, J. F.; Kim, J. K.; J. Am. Chem. Soc. 1970, 92, 7464.
24. RN1 mechanism, see: (a) Rossi, R. A.; Pierini, A. B.; Santiago, A. N. In Organic Reactions; Paquette, L. A., Ed.; Wiley & Sons: New York, 1999; Vol. 54, Chapter 1. (b) Rossi, R. A.; Pierini, A. B.; Penenory, A. B. In The Chemistry of Functional Groups: The Chemistry of Halides, Pseudo-Halides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley & Sons: New York, 1995; Supplement D2, Part 2, Chapter 24. (c) Norris, R. K. In Comprehensive Organic Synthesis; Trost B. M., Ed.; Pergamon Press: New York, 1991; Vol. 4, pp 451-482. (d) Savéant, J.-M. Adv. Phys. Org. Chem. 1990, 26, pp 1-130.
25. RN1 mechanism, see: (a) Rossi, R. A.; Pierini, A. B.; Santiago, A. N. In Organic Reactions; Paquette, L. A., Ed.; Wiley & Sons: New York, 1999; Vol. 54, Chapter 1. (b) Rossi, R. A.; Pierini, A. B.; Penenory, A. B. In The Chemistry of Functional Groups: The Chemistry of Halides, Pseudo-Halides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley & Sons: New York, 1995; Supplement D2, Part 2, Chapter 24. (c) Norris, R. K. In Comprehensive Organic Synthesis; Trost B. M., Ed.; Pergamon Press: New York, 1991; Vol. 4, pp 451-482. (d) Savéant, J.-M. Adv. Phys. Org. Chem. 1990, 26, pp 1-130.
26. RN1 mechanism, see: (a) Rossi, R. A.; Pierini, A. B.; Santiago, A. N. In Organic Reactions; Paquette, L. A., Ed.; Wiley & Sons: New York, 1999; Vol. 54, Chapter 1. (b) Rossi, R. A.; Pierini, A. B.; Penenory, A. B. In The Chemistry of Functional Groups: The Chemistry of Halides, Pseudo-Halides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley & Sons: New York, 1995; Supplement D2, Part 2, Chapter 24. (c) Norris, R. K. In Comprehensive Organic Synthesis; Trost B. M., Ed.; Pergamon Press: New York, 1991; Vol. 4, pp 451-482. (d) Savéant, J.-M. Adv. Phys. Org. Chem. 1990, 26, pp 1-130.
27. RN1 mechanism, see: (a) Rossi, R. A.; Pierini, A. B.; Santiago, A. N. In Organic Reactions; Paquette, L. A., Ed.; Wiley & Sons: New York, 1999; Vol. 54, Chapter 1. (b) Rossi, R. A.; Pierini, A. B.; Penenory, A. B. In The Chemistry of Functional Groups: The Chemistry of Halides, Pseudo-Halides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley & Sons: New York, 1995; Supplement D2, Part 2, Chapter 24. (c) Norris, R. K. In Comprehensive Organic Synthesis; Trost B. M., Ed.; Pergamon Press: New York, 1991; Vol. 4, pp 451-482. (d) Savéant, J.-M. Adv. Phys. Org. Chem. 1990, 26, pp 1-130.
28. (a) Denney, D. B.; Denney, D. Z. Tetrahedron 1991, 47, 6577.
29. (b) Denney, D. B.; Denney, D. Z.; Perez, A. J. Tetrahedron 1993, 49, 4463.
30. (c) Denney, D. B.; Denney, D. Z.; Fenelli, S. P. Tetrahedron 1997, 53, 9835.
31. 16a (16) (a) Bunnett, J. F. Tetrahedron 1993, 49, 4477. (b) Rossi, R. A.; Palacios, S. M. Tetrahedron 1993, 49, 4485. (c) Savéant, J.-M. Tetrahedron 1994, 50, 10117.
32. 16a (16) (a) Bunnett, J. F. Tetrahedron 1993, 49, 4477. (b) Rossi, R. A.; Palacios, S. M. Tetrahedron 1993, 49, 4485. (c) Savéant, J.-M. Tetrahedron 1994, 50, 10117.
33. 16a (16) (a) Bunnett, J. F. Tetrahedron 1993, 49, 4477. (b) Rossi, R. A.; Palacios, S. M. Tetrahedron 1993, 49, 4485. (c) Savéant, J.-M. Tetrahedron 1994, 50, 10117.
34. Zollinger, H. In The Chemistry of Functional Groups: The Chemistry of Triple-Bonded Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley & Sons: New York, 1983; Supplement C, Part 1, Chapter 15, p 619 and references therein.
35. Stoyanovich, F. M.; Marakatkin, M. A.; Gol'dfarb, Ya. L. Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 11, 2537.
36. Flood, D. T. Org. Synth. Collect. Vol. II 1943, 295.
37. Blaschette, A.; Jones, P. G.; Hamann, T.; Naveke, M.; Schomburg, D.; Cammenga, H. K.; Steppuhn, I. Z. Anorg. Allg. Chem. 1993, 619, 912.
38. Barbero, M.; Degani, I.; Fochi, R.; Regondi, V. Gazz. Chim. Ital. 1986, 116, 165.
39. Hendrickson, J. B.; Okano, S.; Bloom, R. K. J. Org. Chem. 1969, 34, 3434.
40. van Zvet, H.; Kooyman, E. C. Rec. Trav. Chim. Pays Bas 1967, 86, 993.
41. 2. No change was observed.
42. Dictionary of Organic Compounds on Cd-ROM, version 7.1; Chapman & Hall Electronic Publishing Division: London, 1999.
43. Vowinkel, E. Synthesis 1974, 430.
44. Chianelli, D.; Testaferri, L.; Tiecco, M.; Tingoli, M. Synthesis 1982, 475.
45. Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1979, 44, 713.
46. Miller, E.; Read, R. R. J. Am. Chem. Soc. 1933, 55, 1224.
47. Landini, D.; Maia, A.; Rampoldi, A. Gazz. Chim. Ital. 1989, 119, 513.
48. King, J. F.; Skonieczny, S.; Poole, G. A. Can. J. Chem. 1983, 61, 235.
49. Cristau, H. J.; Chabaud, B.; Chene, A.; Christol, H. Synthesis 1981, 892.
50. Kunieda, N.; Suzuki, A.; Kinoshita, M.; Imoto, M. Makromol. Chem. 1972, 152, 35.
51. Boeseken, M. J. Rec. Trav. Chim. Pays Bas 1910, 315.
52. Truce, W. E.; Ray, W. J. J. Org. Chem. 1959, 24, 481.