Unexpected conversion of vinyl sulfoxides into carbonyl compounds by means of iodotrimethylsilane

Tetrahedron Letters

Volumn 41, Issue 22, 2000, Pages 4441-4445

  Aversa, Maria C ^a   Barattucci, Anna ^a   Bonaccorsi, Paola ^a   Bruno, Giuseppe ^a   Giannetto, Placido ^a   Policicchio, Manuela ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

Carbonyl compounds; Desulfurization; Iodotrimethylsilane; Sulfoxides

Indexed keywords

CARBONYL DERIVATIVE; DISULFIDE; IODINE DERIVATIVE; SULFOXIDE; TRIMETHYLSILYL DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DESULFURIZATION; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0034622046     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00612-2     Document Type: Article

References (25)

1. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Jones, D. N. J. Org. Chem. 1997, 62, 4376-4384.
2. Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761-3765.
3. The analytical data obtained from this material were consistent with those previously reported by Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166.
4. Eschler, B. M.; Haynes, R. K.; Kremmydas, S.; Ridley, D. D. J. Chem. Soc., Chem. Commun. 1988, 137-138. Pyne, S. G.; Dikic, B. J. Chem. Res. (S) 1990, 226-227. Arai, Y.; Matsui, M.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 1233-1234. Eschler, B. M.; Haynes, R. K.; Ironside, M. D.; Kremmydas, S.; Ridley, D. D.; Hambley, T. W. J. Org. Chem. 1991, 56, 4760-4766. Arai, Y.; Hayashi, K.; Matsui, M.; Koizumi, T.; Shiro, M.; Kuriyama, K. J. Chem. Soc., Perkin Trans. 1 1991, 1709-1716. Arai, Y.; Matsui, M.; Fujii, A.; Kontani, T.; Ohno, T.; Koizumi, T.; Shiro, M. ibid. 1994, 25-39.
5. Eschler, B. M.; Haynes, R. K.; Kremmydas, S.; Ridley, D. D. J. Chem. Soc., Chem. Commun. 1988, 137-138. Pyne, S. G.; Dikic, B. J. Chem. Res. (S) 1990, 226-227. Arai, Y.; Matsui, M.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 1233-1234. Eschler, B. M.; Haynes, R. K.; Ironside, M. D.; Kremmydas, S.; Ridley, D. D.; Hambley, T. W. J. Org. Chem. 1991, 56, 4760-4766. Arai, Y.; Hayashi, K.; Matsui, M.; Koizumi, T.; Shiro, M.; Kuriyama, K. J. Chem. Soc., Perkin Trans. 1 1991, 1709-1716. Arai, Y.; Matsui, M.; Fujii, A.; Kontani, T.; Ohno, T.; Koizumi, T.; Shiro, M. ibid. 1994, 25-39.
6. Eschler, B. M.; Haynes, R. K.; Kremmydas, S.; Ridley, D. D. J. Chem. Soc., Chem. Commun. 1988, 137-138. Pyne, S. G.; Dikic, B. J. Chem. Res. (S) 1990, 226-227. Arai, Y.; Matsui, M.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 1233-1234. Eschler, B. M.; Haynes, R. K.; Ironside, M. D.; Kremmydas, S.; Ridley, D. D.; Hambley, T. W. J. Org. Chem. 1991, 56, 4760-4766. Arai, Y.; Hayashi, K.; Matsui, M.; Koizumi, T.; Shiro, M.; Kuriyama, K. J. Chem. Soc., Perkin Trans. 1 1991, 1709-1716. Arai, Y.; Matsui, M.; Fujii, A.; Kontani, T.; Ohno, T.; Koizumi, T.; Shiro, M. ibid. 1994, 25-39.
7. Eschler, B. M.; Haynes, R. K.; Kremmydas, S.; Ridley, D. D. J. Chem. Soc., Chem. Commun. 1988, 137-138. Pyne, S. G.; Dikic, B. J. Chem. Res. (S) 1990, 226-227. Arai, Y.; Matsui, M.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 1233-1234. Eschler, B. M.; Haynes, R. K.; Ironside, M. D.; Kremmydas, S.; Ridley, D. D.; Hambley, T. W. J. Org. Chem. 1991, 56, 4760-4766. Arai, Y.; Hayashi, K.; Matsui, M.; Koizumi, T.; Shiro, M.; Kuriyama, K. J. Chem. Soc., Perkin Trans. 1 1991, 1709-1716. Arai, Y.; Matsui, M.; Fujii, A.; Kontani, T.; Ohno, T.; Koizumi, T.; Shiro, M. ibid. 1994, 25-39.
8. Eschler, B. M.; Haynes, R. K.; Kremmydas, S.; Ridley, D. D. J. Chem. Soc., Chem. Commun. 1988, 137-138. Pyne, S. G.; Dikic, B. J. Chem. Res. (S) 1990, 226-227. Arai, Y.; Matsui, M.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 1233-1234. Eschler, B. M.; Haynes, R. K.; Ironside, M. D.; Kremmydas, S.; Ridley, D. D.; Hambley, T. W. J. Org. Chem. 1991, 56, 4760-4766. Arai, Y.; Hayashi, K.; Matsui, M.; Koizumi, T.; Shiro, M.; Kuriyama, K. J. Chem. Soc., Perkin Trans. 1 1991, 1709-1716. Arai, Y.; Matsui, M.; Fujii, A.; Kontani, T.; Ohno, T.; Koizumi, T.; Shiro, M. ibid. 1994, 25-39.
9. Eschler, B. M.; Haynes, R. K.; Kremmydas, S.; Ridley, D. D. J. Chem. Soc., Chem. Commun. 1988, 137-138. Pyne, S. G.; Dikic, B. J. Chem. Res. (S) 1990, 226-227. Arai, Y.; Matsui, M.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 1233-1234. Eschler, B. M.; Haynes, R. K.; Ironside, M. D.; Kremmydas, S.; Ridley, D. D.; Hambley, T. W. J. Org. Chem. 1991, 56, 4760-4766. Arai, Y.; Hayashi, K.; Matsui, M.; Koizumi, T.; Shiro, M.; Kuriyama, K. J. Chem. Soc., Perkin Trans. 1 1991, 1709-1716. Arai, Y.; Matsui, M.; Fujii, A.; Kontani, T.; Ohno, T.; Koizumi, T.; Shiro, M. ibid. 1994, 25-39.
10. Becker, S.; Fort, Y.; Caubère, P. J. Org. Chem. 1990, 55, 6194-6198. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Nicolò, F. ibid. 1999, 64, 2114-2118.
11. Becker, S.; Fort, Y.; Caubère, P. J. Org. Chem. 1990, 55, 6194-6198. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Nicolò, F. ibid. 1999, 64, 2114-2118.
12. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Panzalorto, P.; Rizzo, S. Tetrahedron: Asymmetry 1998, 9, 1577-1587.
13. Analytical and spectroscopic data were fully consistent with the assigned structure. NMR studies of the isolated compound 6 showed only the enol form, as depicted in Scheme 1.
14. 3 (3 ml), TMSI 97% (0.8 mmol) was added at rt. The reaction was monitored by TLC. After disappearance of the starting product, MeOH (30 ml) was added and the reaction mixture stirred for 0.5 h, concentrated under reduced pressure, and column chromatographed. The disulfide was eluted first in all cases, followed by the carbonyl compound.
15. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Nicolò, F.; Rizzo, S. Tetrahedron: Asymmetry 1999, 10, 3907-3917.
16. Richter, F.; Kratky, C.; Otto, H. H. Sci. Pharm. 1998, 66, 189-198.
17. The analytical data obtained for our sample of 9 were consistent with those previously reported for its racemic form in Ref. 12.
18. int=0.0161; 318 parameters]. Selected bond distances (Å) and angles (deg): C(1)-N(2)=1.405(8), C(1)-C(9B)=1.52(1), C(1′)-N(3)=1.346(9), C(1′′)-N(2)=1.451(8), C(3)-C(3A)=1.50(1), C(3)-N(2)=1.395(9), C(3A)-C(4)=1.536(9), C(3A)-C(9B)=1.552(9), C(4)-C(5)=1.515(9), C(5)-C(5A)=1.521(9), C(5)-N(1)=1.275(9), C(5A)-C(6)=1.54(1), C(5A)-C(9A)=1.547(9), C(6)-C(7)=1.52(1), C(7)-C(8)=1.53(1), C(8)-C(9)=1.53(1), C(9)-C(9A)=1.530(9), C(9A)-C(9B)=1.527(9), N(1)-N(3)=1.393(8), C(1)-C(9B)-C(9A)=115.2(6), C(1)-N(2)-C(1′′)=121.7(5), C(1)-N(2)-C(3)=113.6(6), C(1′)-N(3)-N(1)=119.1(5), C(1′′)-N(2)-C(3)=124.7(6), C(2′)-C(1′)-N(3)=122.8(6), C(3)-C(3A)-C(4)=108.1(5), C(4)-C(5)-C(5A)=116.0(5), C(4)-C(5)-N(1)=128.3(6), C(5)-N(1)-N(3)=116.4(6), C(5A)-C(5)-N(1)=115.7(6), C(6′)-C(1′)-N(3)=120.3(7), C(1′)-N(3)-N(1)-C(5)=159.3(6), C(2′)-C(1′)-N(3)-N(1)=177.9(6), C(3)-N(2)-C(1′′)-C(6′′)=119.7(8).
19. New compounds 3, 6, 8, 10 were obtained in an analytically pure form and characterized by spectroscopic techniques.
20. For reviews, see: Oae, S.; Uchida, Y. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C., Eds. John Wiley & Sons: New York, 1988; Vol. 15, pp. 583-664. Posner, G. H. ibid. pp. 823-849. Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
21. For reviews, see: Oae, S.; Uchida, Y. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C., Eds. John Wiley & Sons: New York, 1988; Vol. 15, pp. 583-664. Posner, G. H. ibid. pp. 823-849. Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
22. For reviews, see: Oae, S.; Uchida, Y. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C., Eds. John Wiley & Sons: New York, 1988; Vol. 15, pp. 583-664. Posner, G. H. ibid. pp. 823-849. Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
23. For reviews, see: Oae, S.; Uchida, Y. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C., Eds. John Wiley & Sons: New York, 1988; Vol. 15, pp. 583-664. Posner, G. H. ibid. pp. 823-849. Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
24. Solladié, G. Synthesis 1981, 185-196.
25. Following a well-assessed synthetic strategy (Bell, R.; Cottam, P. D.; Davies, J.; Jones D. N. J. Chem. Soc., Perkin Trans. 1 1981, 2106-2115), we prepared 1-phenylethenyl(phenyl)sulfoxide (12) starting from 2-cyanoethyl(phenyl)sulfoxide and phenylacetylene, via the corresponding sulfenic acid.