Different Reactivity Modes of Cis and Trans Di-tert-butylthiiranium Tetrafluoroborates with Water. A New Insight in the Electrophilic Additions to Z and E Di-tert-butylethylenes

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 7018-7020

  Lucchini, Vittorio ^b   Modena, Giorgio ^a   Pasi, Manuela ^a   Pasquato, Lucia ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001059675     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970024x     Document Type: Article

References (25)

1. For easier reading we use the trivial names cis and trans di-tert-butylthiiranium ions for the t-2,t-3- and c-2,t-3-di-tert-butyl-r-l-methylthiiranium ions 1 and 2, respectively.
2. Capozzi, G.; Modena, G.; Pasquato, L. The Chemistry of Sulfenic Acids and Their Derivatives; Patai, S., Ed.; Wiley: Chichester, U.K., 1990; Chapter 10.
3. (a) Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1988, 110, 6900.
4. (b) Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1991, 113, 6600.
5. Modena, G.; Pasquato, L.; Lucchini, V. Phosphorous, Sulfur, Silicon 1994, 95-96, 265.
6. Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1993, 115, 4527. Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1995, 117, 2297.
7. Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1993, 115, 4527. Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1995, 117, 2297.
8. Lucchini, V.; Modena, G.; Pasquato, L. J. Chem. Soc., Chem. Commun. 1994, 1565.
9. Back, T. G. The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; Wiley: Chichester, U.K., 1987; Vol 2, Chapter 3.
10. For bromination, see: Cossi, M.; Persico, M.; Tomasi, J. J. Am. Chem. Soc. 1994, 116, 5373. Ruasse, M.-F. Adv. Phys. Org. Chem. 1993, 28, 207.
11. For bromination, see: Cossi, M.; Persico, M.; Tomasi, J. J. Am. Chem. Soc. 1994, 116, 5373. Ruasse, M.-F. Adv. Phys. Org. Chem. 1993, 28, 207.
12. Harring, S. R.; Edstrom, E. D.; Livinghouse, T. Adv. Heterocycl. Nat. Prod. Synth. 1992, 2, 319. Rayner, C. M. Organosulfur Chemistry. Synthetic Aspects; Page, P., Ed.; Academic Press: London, 1995; Chapter 3.
13. Harring, S. R.; Edstrom, E. D.; Livinghouse, T. Adv. Heterocycl. Nat. Prod. Synth. 1992, 2, 319. Rayner, C. M. Organosulfur Chemistry. Synthetic Aspects; Page, P., Ed.; Academic Press: London, 1995; Chapter 3.
14. For selenium, see, for example: Toshimtsu, A.; Nakano, K.; Mukai, T.; Tamao, K. J. Am. Chem. Soc. 1996, 118, 2756.
15. We used the tetrafluoroborate anion because preliminary experiments with the hexachloroantimonate ion showed a possible attack of water on the anion.
16. Capozzi, G.; DaCol, L.; Lucchini, V.; Modena, G. J. Chem. Soc., Perkin Trans. 2 1980, 68.
17. Raynolds, P.; Zonnebelt, S.; Bakker, S.; Kellogg, R. M. J. Am. Chem. Soc. 1974, 96, 3146.
18. No traces of the E olefin 4, eventually formed from the trans ion 2, generated in turn from the eis isomer 1, could be detected.
19. 2, as reported in ref 3.
20. Press, W. H.; Flannery, B. P.; Teukolsky, S. A.; Vetterling, W. T. Numerical Recipes. The Art of Scientific Computing; Cambridge University Press: Cambridge, U.K., 1986; p 547.
21. Nash, J. C. Compact Numerical Methods for Computers; Adam Hilger Ltd.: Bristol, U.K., 1979; p 141.
22. Dean, C. L.; Garratt, D. G.; Tidwell, T. T.; Schmid, G. H. J. Am. Chem. Soc. 1974, 96, 4958.
23. Ruasse, M. F., Argile, A., Bienvenue-Goëtz, E., Dubois, J. E. J. Org. Chem. 1979, 44, 2758.
24. Fahey, R. C. J. Am. Chem. Soc. 1966, 88, 4681.
25. Huang, X.; Batchelor, R. J.; Einstein, F. W. B.; Bennet, A. J. J. Org. Chem. 1994, 59, 7108.