α-Oxosulfines part 3. Generation and trapping of α-Oxothioaldehyde S- oxides

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 5041-5044

  Capozzi, Giuseppe ^a   Corti, Alessandra ^a   Menichetti, Stefano ^a   Nativi, Cristina ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

OXIDE; PHTHALIMIDE DERIVATIVE; SULFENIC ACID DERIVATIVE; THIOALDEHYDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030765145     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01099-X     Document Type: Article

References (22)

1. Capozzi, G.; Fratini, P.; Menichetti, S.; Nativi, C. Tetrahedron. 1996, 52, 12247-12252.
2. a) Lenz, G. B.; Haltiwanger, R. C; Zwanenburg, B. J. Chem. Soc., Chem Commun., 1984, 502-504.
3. b) Lenz, G. B.; Regeling, H.; van Rozendaal, H. L. M.; Zwanenburg, B. J. Org. Chem. 1985, 50, 2930-2934.
4. a) Freer, A. A.; Kirby, G. W.; Lewis, R. A. J. Chem. Soc, Chem. Commun., 1987, 718-719;
5. b) Kirby, G. W.; McGregor, W. M. J. Chem. Soc, Perkin Trans. 1, 1990, 3175-3181.
6. Capozzi, G.; Menichetti, S.; Nativi, C.; Rosi, A.; Valle, G. Tetrahedron. 1992, 48, 9023-9032.
7. a) Capozzi, G.; Menichetti, S.; Nativi, C.; Rosi, A.; Franck, R. W. Tetrahedron Lett. 1993, 34, 4253-4256.
8. b) Capozzi, G.; Franck, R. W. G.; Mattioli, M.; Menichetti, S.; Nativi, C.; Valle, G. J. Org. Chem., 1995, 60, 6416-6426.
9. Capozzi, G.; Menichetti, S.; Nativi, C.; Simonti, M-C., Tetrahedron Lett. 1994, 35, 9451-9454.
10. Derivatives 2e and 2f were obtained reacting 1 with the appropriate silyl enol ether in dichloromethane at -18 °C.
11. a) Nakayama, J.; Mizumura, A. Tetrahedron Lett., 1995, 36, 8583-8586.
12. b) Haake, M.; Benack, H. Synthesis, 1976, 308-310.
13. c) Haake, M.; Gebbing, H.; Benack, H. Synthesis, 1979, 97-98
14. a) Harpp, D. N. ; Back, T. G. Tetrahedron Lett., 1972, 52, 5313-5316.
15. b) Harpp, D. N.; Back, T. G. J. Org. Chem., 1973, 38, 4328-4334.
16. 2b who described a number of similar dihydrothiopyran derivatives including 6b and 6d.
17. Capozzi, G.; Fratini, P.; Menichetti, S.; Nativi, C. Tetrahedron. 1996, 52, 12233-12246.
18. Capozzi, G., Fratini, P., Menichetti, S., Nativi, C. Tetrahedron. Lett., 1995, 36, 5089-5092
19. Independent oxidation of cis and trans cycloadduct 8a gave the same sulfone indicating that cis-8a and trans-8a must be stereoisomers at sulfoxide sulfur.
20. 11
21. 3S: C, 60.48; H, 5.92. Found: C, 60.00; H, 6.03.
22. Ab initio calculations were obtained using a 3-21G* basis set with a geometry optimisation implemented via a Spartan program running on a IBM-RISC 6000 work station.