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Volumn 40, Issue 19, 1999, Pages 3785-3788

Thiophene sulfoximides: 2,4- and 3,4-di-tert-butyl-1-imino-1,1- dihydrothiophene 1-oxides

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DI TERT BUTYL 1 IMINO 1,1 DIHYDROTHIOPHENE 1 OXIDE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033532233     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00609-7     Document Type: Article
Times cited : (19)

References (29)
  • 1
    • 0001649254 scopus 로고
    • Ed. by D. N. Jones, Pergamon Press
    • [1] For reviews, see for example a) C. R. Johnson, Comprehensive Organic Chemistry, Ed. by D. N. Jones, Vol. 3. Pergamon Press, 1979, Part 11.11 (p. 223);
    • (1979) Comprehensive Organic Chemistry , vol.3 , Issue.PART 11.11 , pp. 223
    • Johnson, C.R.1
  • 11
    • 0013521705 scopus 로고    scopus 로고
    • All new compounds gave satisfactory elemental analysis results
    • [8] All new compounds gave satisfactory elemental analysis results.
  • 12
    • 0013491582 scopus 로고    scopus 로고
    • note
    • 3) δ 27.7, 29.6, 33.1, 35.1, 120.1, 122.8, 152.7, 156.0.
  • 17
    • 0013530676 scopus 로고    scopus 로고
    • CHIRALPAK AD (4.6 mm i.d. x 250 mm; Daicel Chemical Industries, Ltd) was used with hexane/ethanol (98.5/1.5) as the eluent (flow rate: 1.0 ml/min, detector: UV, 254 nm)
    • [12] Chiralpak Ad (4.6 mm i.d. x 250 mm; Daicel Chemical Industries, Ltd) was used with hexane/ethanol (98.5/1.5) as the eluent (flow rate: 1.0 ml/min, detector: UV, 254 nm).
  • 18
    • 0013555614 scopus 로고
    • [13] The sulfur atom of the sulfoxide 4 is also chiral. However, the pyramidal inversion energy of thiophene 1-oxides is not sufficiently large that optical resolution of a pair of enantiomers at room temperature must be impossible: calculated and experimental pyramidal inversion energies are 13.3 and 14.8 kcal/mol for 2,5-dimethylthiophene and 2,5-di-tert-octylthiophene 1-oxides, respectively; a) J. D. Andose, A. Rauk, R. Tang, and K. Mislow, Int. J. Sulfur Chem., 1971, A1, 66;
    • (1971) Int. J. Sulfur Chem. , vol.A1 , pp. 66
    • Andose, J.D.1    Rauk, A.2    Tang, R.3    Mislow, K.4
  • 19
    • 0000216705 scopus 로고
    • Indeed, attempted isolation of a pair of enantiomers of 4 by HPLC on a chiral column failed
    • b) W. L. Mock, J. Am. Chem. Soc., 1970, 92, 7610. Indeed, attempted isolation of a pair of enantiomers of 4 by HPLC on a chiral column failed.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 7610
    • Mock, W.L.1
  • 21
    • 0013549034 scopus 로고    scopus 로고
    • note
    • 16
  • 27
    • 84977291953 scopus 로고
    • e) G. Douglas, C. S. Frampton, and K. W. Muir, Acta Cryst., 1993, C49, 1197. For a congested thiophene 1,1-dioxide, A. W. Krebs, E. Franken, M. Müller, H. Colberg, W. Cholcha, J.Wilken, J. Ohrenberg, R. Albrecht, and E. Weiss, Tetrahedron Lett., 1992, 33, 5947.
    • (1993) Acta Cryst. , vol.C49 , pp. 1197
    • Douglas, G.1    Frampton, C.S.2    Muir, K.W.3
  • 29
    • 0013529949 scopus 로고    scopus 로고
    • We thank Dr. T. Fujihara for his help in determination of the CD spectra
    • [18] We thank Dr. T. Fujihara for his help in determination of the CD spectra.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.