Formation of cyclic sulfonium salts by Me3SiI-promoted intramolecular displacement of hydroxide or methoxide by sulfide. Ring contraction thiepane → thiolane

Tetrahedron

Volumn 52, Issue 16, 1996, Pages 5989-5998

  Cerè, Vanda ^a   Pollicino, Salvatore ^a   Fava, Antonino ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSULFUR DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029879829     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00229-3     Document Type: Article

References (21)

1. For a review on the use of this reagent: Olah, G. A.; Narang, S. C. Tetrahedron 1982, 38, 2225-2277.
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3. Jung, M. E.; Lyster; M. A: J. Org. Chem. 1977, 42, 3761-3764.
4. Reese, C. B. in "Protective Groups in Organic Chemistry", J. F. W. McOmie, Ed., Plenum Press, London, 1973, pp 95-143.
5. a) Schmidt, A. H.; Russ, M. Chem. Z, 1978, 102, 26.
6. b) Olah, G. A.; Narang; S. C.; Gupta, B. G. B.; Malhotra, R. Synthesis, 1979, 61-62;
7. c). id. J. Org. Chem. 1979, 44, 1247-1251.
8. d) Bhatt, M. V; Kul karni, S. U. Synthesis, 1983, 249-282.
9. a) Capon, B. Quart. Rev. 1964, 18, 45-111;
10. b). Capon, B.; McManus, S. P. in Neighboring Group Participation, Plenum Press, New York 1976, Vol. 1, Chapter 5.
11. Ikegami; S.; Asai, T.; Tsuneoka, K.; Matsumura, S.; Akaboshi, S. Tetrahedron 1974, 30, 2087-2092.
12. 9 Experiments are under way to resolve this ambiguity.
13. a) Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701-704;
14. b) Mandolini, L. Advances in Physical Organic Chemistry, Academic Press, London 1986, p 1-111.
15. Molecular mechanics calculations (MMX force field, from Serena Software) indicate cisthiahydrindane to be less stable than the trans isomer by ≈ 1.8 kcal/mol.
16. Cerè, V.; Guenzi, A; Pollicino, S.; Sandri, E.; Fava, A. J. Org. Chem. 1980, 45, 261-264.
17. Kirner, W. R; Holmes Richter, G. J. Am. Chem. Soc. 1929, 51, 3409-3418.
18. 4 reduction resulted in a sizeable loss of deuterium.
19. Amouroux, R.; Jatczar, M.; Chastrette, M. Bull, Soc. Chim: France, 1987, 505-510.
20. Overberger, C. G.; Katchman, A. J. Am. Chem. Soc. 1956, 78, 1965-1968
21. The crude mixture of sulfide and sulfonium salt, derived from the hydroxy or methoxy sulfides, was separated by extraction with light petroleum ether.