Thioacrolein S-oxide

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1385-1388

  Pelloux Léon, Nadia ^a   Arnaud, Roger ^a   Ripoll, Jean Louis ^b   Beslin, Pierre ^b   Vallée, Yannick ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; THIOACROLEIN S OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; THERMODYNAMICS;

EID: 0031584944     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00026-9     Document Type: Article

References (26)

1. 1. Block, E.; Penn, R. E.; Olsen, R. J.; Sherwin, P. F. J. Am. Chem. Soc., 1976, 98, 1264-1265.
2. 2. Vallée, Y.; Ripoll, J. L.; Lafon, C.; Pfister-Guillouzo, G. Can. J. Chem., 1986, 65, 290-291.
3. 3. Block, E. Angew. Chem., Int. Ed. Engl., 1992, 31, 1135-1178.
4. 4. Zwanenburg, B. Recl. Trav. Chim. Pays-Bas, 1982, 101, 1-27. Metzner, P. Phosphorus Sulfur Silicon, 1991, 59, 1-16.
5. 4. Zwanenburg, B. Recl. Trav. Chim. Pays-Bas, 1982, 101, 1-27. Metzner, P. Phosphorus Sulfur Silicon, 1991, 59, 1-16.
6. 5. Bock, H.; Solouki, B.; Mohmand, E.; Block, E.; Revelle, L. K. J. Chem. Soc., Chem. Comun., 1977, 287-288.
7. 6. Penn, R. E.; Olsen, R. J. J. Mol. Spectrosc., 1976, 61, 21-28. Powers, D. E., Arrington, C. A.; Harris, W. C.; Block, E.; Kalasinsky, V. F. J. Phys. Chem., 1979, 83, 1890-1892.
8. 6. Penn, R. E.; Olsen, R. J. J. Mol. Spectrosc., 1976, 61, 21-28. Powers, D. E., Arrington, C. A.; Harris, W. C.; Block, E.; Kalasinsky, V. F. J. Phys. Chem., 1979, 83, 1890-1892.
9. 7. Vallée, Y. Reviews Heteroatom Chem., 1993, 8, 1-20.
10. 8. Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett., 1980, 21, 2421-2424.
11. 9. Giles, H. G.; Marty, R. A.; de Mayo, P. Can. J. Chem., 1976, 54, 537-542. Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber., 1982, 115, 1339-1348. Beslin, P. Heterocyclic Chem., 1983, 20, 1753-1754.
12. 9. Giles, H. G.; Marty, R. A.; de Mayo, P. Can. J. Chem., 1976, 54, 537-542. Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber., 1982, 115, 1339-1348. Beslin, P. Heterocyclic Chem., 1983, 20, 1753-1754.
13. 9. Giles, H. G.; Marty, R. A.; de Mayo, P. Can. J. Chem., 1976, 54, 537-542. Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber., 1982, 115, 1339-1348. Beslin, P. Heterocyclic Chem., 1983, 20, 1753-1754.
14. 10. For an attempt to obtain 1 which in fact efficiently gave thioacrolein, see: Block, E.; Zao, S. H. Tetrahedron Lett., 1990, 31, 5003-5007. For metal complexes of 1, see: Dittner, D. C.; Takahashi, K.; Iwanami, M.; Tsai, A. I.; Chang, P. L.; Blidner, B. B.; Stamos, I. K. J. Am. Chem. Soc., 1976, 98, 2795-2803.
15. 10. For an attempt to obtain 1 which in fact efficiently gave thioacrolein, see: Block, E.; Zao, S. H. Tetrahedron Lett., 1990, 31, 5003-5007. For metal complexes of 1, see: Dittner, D. C.; Takahashi, K.; Iwanami, M.; Tsai, A. I.; Chang, P. L.; Blidner, B. B.; Stamos, I. K. J. Am. Chem. Soc., 1976, 98, 2795-2803.
16. 11. Gaussian 94 (Revision A.1), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery , J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrewski, V. G.; Ortiz, J. V.; Foresmen, J. B.; Cioslowski, B.; Stefanov, B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J.S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian Inc. Pittsburgh PA 1995.
17. Z was then found 27.2 kcal/mol higher and 3 7.9 kcal/mol lower, than 1(Z). These results are close to those obtained with MP2 geometries. Ruttnik, P. J. A.; Burgers, P. C.; Francis, J. T.; Terlouw, J. K. J. Phys. Chem., 1996, 100, 9694-9697.
18. 13. Pelloux, N.; Vallée, Y.; Duchenet, V. Phosphorus Sulfur Silicon, 1994, 89, 17-23.
19. 14. Pine, S. H.; Shen, G. S.; Hoang, H. Synthesis, 1991, 165-167.
20. 2C=CH), 7.2-7.5 (m, ArH) ; 7(E) was characterized by a doublet at 3.49 ppm (J = 8.2 Hz).
21. -1.
22. C=S-0 vibration.
23. 18. Block, E.; Revelle, L. K.; Bazzi, A. A. Tetrahedron Lett., 1980, 21, 1277-1280.
24. 13C NMR spectrum was ca. 14/1. Thus, we cannot exclude the presence of small amounts (no more than 7%) of 3 and/or 4.
25. 20. Comparison of the spectrum with the one reported for the parent heterocycle 3,4-dihydro-2H-thiopyran S-oxide also points to structure 8 : Crumbie, R. L.; Ridley, D. D.; Steel, P. J. Aust. J. Chem., 1985, 38, 119-132.
26. 21. A more complete ab initio study of sulfines is now under investigation in Grenoble. In particular, we are studying this cycloaddition from a theoretical point of view.