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Volumn 49, Issue 39, 2008, Pages 5642-5644

Direct aromatization of chlorohydroazulenones with triflic anhydride: access to chloroazulenyl triflates

Author keywords

Azulenes; Cross coupling reactions; Direct aromatization; Hydroazulenones; Triflic anhydride

Indexed keywords

BENZENE DERIVATIVE; CHLOROHYDROAZULENONE DERIVATIVE;

EID: 49349085135     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.072     Document Type: Article
Times cited : (4)

References (32)
  • 9
    • 49349106780 scopus 로고    scopus 로고
    • Slavtcheff, C. S.; Barrow, S. R.; Kanga, V. D.; Cheney, M. C.; Znaiden A. (Unilever PLC, UK) WO9503779, 1995; Chem. Abstr. 1995, 123, 17488w.
    • Slavtcheff, C. S.; Barrow, S. R.; Kanga, V. D.; Cheney, M. C.; Znaiden A. (Unilever PLC, UK) WO9503779, 1995; Chem. Abstr. 1995, 123, 17488w.
  • 21
    • 49349087663 scopus 로고    scopus 로고
    • note
    • AB = 24 Hz, 2H), 2.53-2.65 (m, 1H), 1.27 (d, J = 7.3 Hz, 3H).
  • 22
    • 49349100595 scopus 로고    scopus 로고
    • note
    • By addition of lutidine to the reaction mixture containing 5b at -10 °C, the yield of isolated chloroazulene 2b was 33%.
  • 23
    • 49349102096 scopus 로고    scopus 로고
    • note
    • 4. Purification by dry silica gel column chromatography with pentane gave 146 mg (81%) of chloroazulene 2b (see Ref. 3).
  • 25
    • 49349093428 scopus 로고    scopus 로고
    • note
    • The yields were identical using triphenylcarbenium, but the purification was more difficult.
  • 27
    • 49349114105 scopus 로고    scopus 로고
    • note
    • +] 324.9908, found 324.9916.
  • 30
    • 49349085430 scopus 로고    scopus 로고
    • note
    • +] 191.0622, found 191.0620.
  • 31
    • 49349112534 scopus 로고    scopus 로고
    • note
    • Chlorotrienone 1a is obtained in 2 steps from cycloheptatriene in 45% overall yield. Chlorine reduction in 2a is achieved in 92% yield (see Ref. 3).
  • 32
    • 49349109500 scopus 로고    scopus 로고
    • note
    • Chlorotrienone 1b is obtained from the tropylium cation in 43% overall yield (see Ref. 4b). Chlorine/methyl exchange in 2b is achieved in 98% to give the 1,4-dimethylazulene (see Ref. 3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.