Synthesis and characterization of thiophene 1-oxides kinetically stabilized by bulky substituents at the 3- and 4-positions

Chemistry Letters

Volumn , Issue 6, 1997, Pages 499-500

  Nakayama, Juzo ^a   Yu, Ting ^a   Sugihara, Yoshiaki ^a   Ishii, Akihiko ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031536794     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.499     Document Type: Article

References (19)

1. For a review, see J. Nakayama and Y. Sugihara, Sulfur Reports, 19, 349 (1997).
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8. N. Furukawa, S. Zang, S. Sato, and M. Higaki, Heterocycles, 44, 61 (1997). See also M. Higaki and N. Furukawa, 24th Congress of Helerocyclic Chemistry, Osaka, November, 1993, Book of Abstracts, p. 277.
9. Prepared by treatment of 3,4-di-t-butyl-2,5-dilithiothiophene with trimethylsilyl chloride.
10. Satisfactory elemental analyses were obtained for all new compounds.
11. +).
12. Such desililation was previously encountered in the oxidation of trimethylsilyl substituted thiophcnes with m-CPBA: see S. Gronowitz, G. Nikitidis, and A. Hallberg, acta Chem. Scand., 45, 632 (1991); S. Gronowitz, G. Nikitidis, A. Hallberg, and C. Stalhandske, Acta Chem. Scand., 45, 636 (1991).
13. Such desililation was previously encountered in the oxidation of trimethylsilyl substituted thiophcnes with m-CPBA: see S. Gronowitz, G. Nikitidis, and A. Hallberg, acta Chem. Scand., 45, 632 (1991); S. Gronowitz, G. Nikitidis, A. Hallberg, and C. Stalhandske, Acta Chem. Scand., 45, 636 (1991).
14. 1H NMR (α-hydrogen signal, δ 6.75), but its isolation in pure form was unsatisfactory.
15. For structure prediction of the parent thiophene 1-oxide by calculations, see: J. A. Hashmall, V. Horak, L. E. Khoo, C. Q. Quicksall, and M. K. Sun, J. Am. Chem Soc., 103, 289 (1981); I. Rozas, J. Phys. Org. Chem., 5, 74 (1992).
16. For structure prediction of the parent thiophene 1-oxide by calculations, see: J. A. Hashmall, V. Horak, L. E. Khoo, C. Q. Quicksall, and M. K. Sun, J. Am. Chem Soc., 103, 289 (1981); I. Rozas, J. Phys. Org. Chem., 5, 74 (1992).
17. 3 Z = 4, R = 0.044, wR = 0.051, 4242 independent reflections.
18. K. W. Buck, A. B. Foster, W. D. Pardle, M. H. Qadir, and J. M. Webber, Chem. Commun., 1996, 758; D. J. H. Smith, J. D. Finlay, C. R. Hall, and J. J. Uebel, J. Org. Chem., 44, 4757 (1979).
19. K. W. Buck, A. B. Foster, W. D. Pardle, M. H. Qadir, and J. M. Webber, Chem. Commun., 1996, 758; D. J. H. Smith, J. D. Finlay, C. R. Hall, and J. J. Uebel, J. Org. Chem., 44, 4757 (1979).