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Volumn , Issue 1, 2006, Pages 128-132

1-(Trifluoromethyl)vinylation via oxirane or oxetane ring-opening: A facile synthesis of 4- or 5-hydroxy-functionalized 2-trifluoromethyl-1-alkenes

Author keywords

(Trifluoromethyl)vinyl group; Lithium halogen exchange; Oxirane; Ring opening; Unsaturated alcohol

Indexed keywords

ALCOHOLS; ETHERS; LITHIUM COMPOUNDS; OLEFINS; VINYL RESINS;

EID: 30944457082     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918413     Document Type: Article
Times cited : (17)

References (39)
  • 4
    • 30944439107 scopus 로고    scopus 로고
    • and references therein
    • Lebel, H.; Paquet, V. Org. Lett. 2002, 4, 1674; and references therein.
    • (2002) Org. Lett. , vol.4 , pp. 1674
    • Lebel, H.1    Paquet, V.2
  • 16
    • 0021130585 scopus 로고
    • For reports on 1-(trifluoromethyl)vinyl palladium species generated via oxidative addition of 2, see: (a) Fuchikami, T.; Yamanouchi, A.; Ojima, I. Synthesis 1984, 766.
    • (1984) Synthesis , pp. 766
    • Fuchikami, T.1    Yamanouchi, A.2    Ojima, I.3
  • 31
    • 30944444370 scopus 로고    scopus 로고
    • note
    • 2 and then 2-phenethyloxirane (0.8 mmol) at -78 °C. After the mixture was stirred for 30 min, phosphate buffer was added to quench the reaction. Usual work-up followed by column chromatography on silica gel gave 1,4-diphenylbutan-2-ol (the phenyl adduct: 139 mg, 77%) and 1-phenyloctan-3-ol (the butyl adduct: 20 mg, 12%).
  • 32
    • 0003082961 scopus 로고
    • For reports on the synthesis of 3-(trifluoromethyl)homoallylic alcohols, see: (a) Yamazaki, T.; Ishikawa, N. Chem. Lett. 1984, 521.
    • (1984) Chem. Lett. , pp. 521
    • Yamazaki, T.1    Ishikawa, N.2
  • 35
    • 30944449805 scopus 로고    scopus 로고
    • note
    • 2 (1.0 equiv) did not cause a considerable change in the ratio of 3 and 4.
  • 37
    • 30944452816 scopus 로고    scopus 로고
    • note
    • 2-Phenethyloxirane was prepared by oxidation of 4-phenyl-but-1-ene with MCPBA.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.