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Volumn , Issue 2, 2005, Pages 247-250

Aromatic ring-opening of 2-fluorobenzothiophenes by alkyllithiums

Author keywords

Addition to sulfur; Alkyllithium reagents; Benzothiophenes; Fritsch Buttenberg Wiechell rearrangements; Ring opening

Indexed keywords

1 FLUOROVINYL DERIVATIVE; 2 FLUOROBENZOTHIOPHENE DERIVATIVE; ACETYLENE DERIVATIVE; ALKYL GROUP; ANION; AROMATIC COMPOUND; BENZOTHIOPHENE DERIVATIVE; DIPHENYLACETYLENE DERIVATIVE; LITHIUM DERIVATIVE; REAGENT; SULFUR; THIOPHENE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 13844292454     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837230     Document Type: Article
Times cited : (20)

References (26)
  • 6
  • 7
    • 13844267086 scopus 로고    scopus 로고
    • note
    • 20 to yield 5a.
  • 8
    • 0035826341 scopus 로고    scopus 로고
    • The reverse of this reaction, the synthesis of benzothiophenes from phenylacetylenes, has been reported by: (a) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651.
    • (2001) Org. Lett. , vol.3 , pp. 651
    • Flynn, B.L.1    Verdier-Pinard, P.2    Hamel, E.3
  • 11
    • 13844281865 scopus 로고    scopus 로고
    • note
    • The first step was found to be rate limiting based on the following observations. 1) The FBW rearrangement was reported repeatedly to occur rapidly and at temperature below -20 °C. 2) We haven't been able to isolate any of the non-rearranged products from the intermediate 2,2-diaryl-1- fluorovinyllithium 8, even when the reaction was quenched at -78 °C (first entry in Table 1). 3) In most reactions where there is no diphenylacetylene produced, the major product isolated is the starting benzothiophene 7.
  • 21
    • 13844280600 scopus 로고    scopus 로고
    • note
    • 8ClFS: C, 64.00; H, 3.07. Found: C, 64.45; H, 3.00.
  • 23
    • 13844276293 scopus 로고    scopus 로고
    • note
    • 2-Chloro-3-phenylbenzothiophene was prepared in 64% yield from 9a by lithiation with BuLi at -78 °C followed by reaction with N-chlorosuccinimide.
  • 24
    • 13844257043 scopus 로고    scopus 로고
    • note
    • The same reaction with s-BuLi yielded only 3-phenylbenzothiophene 13.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.