On the structure of intermediate adducts arising from dithionite reduction of pyridinium salts: A novel class of derivatives of the parent sulfinic acid

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1235-1240

  Carelli, Vincenzo ^a   Liberatore, Felice ^a   Scipione, Luigi ^a   Musio, Roberta ^b   Sciacovelli, Oronzo ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF BARI   (Italy)

Author keywords

13C and 17O NMR spectroscopy; Dithionite reduction; Parent sulfinic acid derivatives; Pyridinium salts

Indexed keywords

DITHIONITE; PYRIDINIUM DERIVATIVE; SULFINIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS;

EID: 0034685217     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02251-0     Document Type: Article

References (36)

1. Warburg, O.; Christian, W.; Griese, A. Biochem. Z. 1935, 282, 157.
2. Yarmolinsky, M. B.; Colowick, S. P. Biochim. Biophys. Acta 1956, 20, 177.
3. Sutter-Kostic, K.; Carrer, P. Helv. Chim. Acta 1956, 39, 677.
4. Wallenfels, K.; Schüly, H. Justus Liebig Ann. Chem. 1959, 621, 178.
5. Kosower, E. M.; Bauer, S. J. Am. Chem. Soc. 1960, 82, 2191.
6. Caughey, W. S.; Shellenberg, K. A. J. Org. Chem. 1966, 31, 1978.
7. Biellmann, J. F.; Callot, H. J. Tetrahedron Lett. 1966, 7, 3991.
8. Biellmann, J. F.; Callot, H. J. Bull. Soc. Chim. Fr. 1968, 1154.
9. Blankenhorn, G.; Moore, E. G. J. Am. Chem. Soc. 1980, 102, 1092.
10. Roberts, R. M. G.; Ostovic, D.; Kreevoy, M. M. J. Org. Chem. 1983, 48, 2053.
11. (a) Carelli, V.; Liberatore, F.; Tortorella, S.; Micheletti-Moracci, F. Gazz. Chim. Ital. 1983, 113, 569.
12. (b) Carelli, V.; Liberatore, F.; Casini, A.; Di Rienzo, B.; Tortorella, S.; Scipione, L. New J. Chem. 1996, 20, 125.
13. (c) Carelli, V.; Liberatore, F.; Scipione, L.; Impicciatore, M.; Barocelli, E.; Cardellini, M.; Giorgioni, G. J. Control Release 1996, 42, 209.
14. 13C NMR studies the adduct preparation was carried out directly in NMR tubes. All spectra were recorded at 11.4 tesla on a Bruker AM 500 spectrometer.
15. Butt, G. L.; Deady, L. W. J. Heterocycl. Chem. 1984, 21, 981.
16. Bossaert, J. D.; Domisse, R. A.; Alderweireldt, F. C.; Gerlings, P. J. Chem. Res. (Miniprint) 1987, 2360.
17. Micheletti-Moracci, F.; Liberatore, F.; Carelli, V.; Arnone, A.; Carelli, I.; Cardinali, M. E. J. Org. Chem. 1978, 43, 3420.
18. Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Tabellen zur Strukturaufklärung Organischer Verbindungen mit Spektroskopichen Methoden; Springer: Berlin, Heidelberg, 1976; C45.
19. 13C NMR Spectroskopie; Georg Thieme: Stuttgart, 1977; pp. 52-54.
20. Schneider, H. J.; Hoppen, V. J. Org. Chem. 1978, 43, 3866.
21. (a) Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899.
22. (b) Thiel, W. QCPE 1982, 438.
23. (c) Musio, R. QCPE Bulletin 1997, 17, 41.
24. Pople, J. A.; Schneider, W. G.; Bernstein, H. J. High-Resolution Nuclear Magnetic Resonance; McGraw-Hill: New York, 1959; p. 175.
25. 2O respectively.
26. (a) Barbarella, G. J. Mol. Struct. 1989, 186, 197.
27. (b) Hellier, D. G.; Liddy, H. G. Mag. Res. Chem. 1988, 26, 671.
28. (c) Hellier, D. G.; Liddy, H. G. Mag. Res. Chem. 1989, 27, 431.
29. (d) O-17 NMR Spectroscopy in Organic Chemistry; Boykin, D. W., Ed.; CRC Press: Boca Raton, FL, 1991.
30. Dahn, H.; Van Toan, V.; Ung-Truong, M. N. Mag. Res. Chem. 1991, 29, 897.
31. Chang, S.; Le Noble, W. J. J. Am. Chem. Soc. 1983, 105, 3708.
32. (a) Bugner, D. E. J. Org. Chem. 1989, 54, 2580.
33. (b) Musio, R.; Sciacovelli, O. J. Org. Chem. 1997, 62, 9031.
34. Dunitz, J. D. Acta Cryst. 1956, 9, 579.
35. Horner, D. A.; Connick, R. Inorg. Chem. 1986, 25, 2414.
36. Meek, J. S.; Fowler, J. S. J. Org. Chem. 1958, 33, 3422.