An easy and practical synthesis of symmetrical thiosulfonic S-esters

Synlett

Volumn , Issue 8, 1998, Pages 894-896

  Chemla, Fabrice ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009448980     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1798     Document Type: Article

References (24)

1. For a review, see : Zefirov, M.S.; Zyk, N.V.; Beloglazkina, E.K.; Kutateladze, A.G.K. Sulfur Reports 1993, 14, 223.
2. Trost, B.M. Chem. Rev. 1978, 78, 363;
3. Palumbo, G.; Ferreri, C.; D'Ambrosio, C.; Caputo, R. Phosph. & Sulfur 1984, 19, 235, and references cited therein.
4. For a recent example, see : Arterburn, J.B.; Perry, M.C.; Nelson, S.L.; Dible, B.R.; Holguin, M.S. J. Am. Chem. Soc. 1997, 119, 9309.
5. For a preparation of methanethiosulfonic acid, methyl ester 4e from DMSO, see : Lazlo, P.; Mathy, A. J. Org. Chem. 1984, 49, 2281; for a preparation of symmetrical thiosulfonic esters from sulfinyl chlorides, see reference 13.
6. Palumbo, G.; Caputo, R. Synthesis 1981, 888.
7. Karrer, P.; Wehrli, W.; Biedermann, E.; dallaVedova, M. Helv. Chim. Acta 1928, 11, 233.
8. Xia, M.; Chen, Z. Synth. Commun. 1997, 27, 1309.
9. Meier, H.; Menzel, I. Synthesis 1972, 267.
10. Chemla, P.; Normant, J.F. Tetrahedron 1997, 53, 17265.
11. Disulfones were identified (except for 6, see ref 14) by comparison with described spectral data : Bartmann, E.A. Synthesis 1993, 490.
12. Klivenyi, F.; Vinkler, E.; Lazar, J. Acta Chim. Acad. Sci. Hung. 1965, 46, 357.
13. 3, 100MHz): δ 142.77, 136.50, 133.77, 131.48, 129.47, 128.86, 127.80, 127.45; these data are identical to those previously reported : Billard, T.; Langlois, B.R.; Large, S.; Anker, D.; Roidot, N.; Roure, P. J. Org. Chem. 1996, 61, 7545.
14. 3, 100MHz): δ 20.70, 18.48; ; these data are identical to those previously reported : : Lazlo, P.; Mathy, A. J. Org. Chem. 1984, 49, 2281.
15. -1 ; mp = 112°C.
16. 3, 100MHz): δ 144.78, 142.17, 140.33, 136.49, 130.30, 129.48, 125.58, 124.52, 21.61, 21,43; these data are identical to those previously reported : Davis, F.A.; Reddy, R.E.; Sczewczyk, J.M. J. Org. Chem. 1995, 60, 7037.
17. 3, 400MHz) : δ 7.1 (s, 2H), 7.0 (s, 2H); 3.72 (hept, 2H, J=8Hz), 3.60 (hept, 2H, J=8Hz), 2.91 (m, 2H), 1.1-1.3 (m, 24H); these data are consistent with those previously reported : Adlington, R.M.; Barrett, A.G.M. J. Chem. Soc., Perkin Trans. I 1980, 1076.
18. 3, 100MHz): δ 163.65, 163.32, 138.46, 134.98, 129.99, 118.99, 115.03, 113.95, 55.83, 55.59; ; these data are identical to those previously reported : Bell, K.H. J. Chem. Soc., Perkin Trans. I 1988, 1957.
19. 3, 100MHz): δ 64.65, 38.47, 23.54, 17.73, 13.50, 13.02; these data are identical to those previously reported : Smith, D.J.; Maggio, E.T.; Kenyon, G.L. Biochemistry 1975, 14, 166.
20. 3, 100MHz): δ 55.55, 38.59, 24.46, 16.49. These data are consistent with those previously reported : Derbesy, G.; Harpp, D.N. J. Org. Chem. 1995, 60, 1044.
21. DeLucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157.
22. Freeman, F.; Bartosik, L.G.; vanBui, N.; Keindl, M.C.; Nelson, E.L. Phosph. & Sulfur 1988, 35, 375;
23. Freeman, F. Chem. Rev. 1984, 84, 117;
24. Freeman, F.; Keindl, M.C. Synthesis 1983, 913.