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Volumn 69, Issue 7, 2004, Pages 2381-2385

Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624 B

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; QUENCHING; SYNTHESIS (CHEMICAL);

EID: 1842608758     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0351217     Document Type: Article
Times cited : (88)

References (30)
  • 3
    • 33947088987 scopus 로고
    • For reviews of the halogen dance reaction, see: (a) Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139.
    • (1972) Acc. Chem. Res. , vol.5 , pp. 139
    • Bunnett, J.F.1
  • 5
    • 85013565512 scopus 로고
    • Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York
    • (c) Fröhlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol 6, pp 1-35.
    • (1994) In Progress in Heterocyclic Chemistry , vol.6 , pp. 1-35
    • Fröhlich, J.1
  • 18
    • 1842552632 scopus 로고    scopus 로고
    • note
    • For leading references on the mechanism of this reaction, see ref 4 and references therein.
  • 19
    • 85082508646 scopus 로고
    • For examples of halogen dance reactions that are driven by differential acidities on thiophenes, see ref 11a and the following: Sauter, F.; Fröhlich, H.; Kalt, W. Synthesis 1989, 771.
    • (1989) Synthesis , pp. 771
    • Sauter, F.1    Fröhlich, H.2    Kalt, W.3
  • 20
    • 0000889418 scopus 로고
    • For a review of the chemistry of lithio thiazole, see: Iddon, B. Heterocycles 1995, 41, 533.
    • (1995) Heterocycles , vol.41 , pp. 533
    • Iddon, B.1
  • 21
    • 0000107780 scopus 로고
    • For other examples where an in situ trapping with a silyl chloride proceeds faster than a halogen dance, see: (a) Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. Heterocycles 1983, 20, 2035.
    • (1983) Heterocycles , vol.20 , pp. 2035
    • Kano, S.1    Yuasa, Y.2    Yokomatsu, T.3    Shibuya, S.4
  • 25
    • 0032447309 scopus 로고    scopus 로고
    • For a review of nucleophilic reactions of 2-lithiothiazole, see: Dondoni, A. Synthesis 1998, 1681.
    • (1998) Synthesis , pp. 1681
    • Dondoni, A.1
  • 28
    • 1842604836 scopus 로고    scopus 로고
    • note
    • This reaction requires prior purification of the anhydride by recrystallization from ethyl acetate in order to minimize the formation of several byproducts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.