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Volumn 45, Issue 29, 2004, Pages 5669-5671

A homologous enolate Truce-Smiles rearrangement

Author keywords

Rearrangement; Truce Smiles

Indexed keywords

2 HYDROXYACETOPHENONE; ACETOPHENONE DERIVATIVE; DIPHENYL ETHER DERIVATIVE; FLUORINE DERIVATIVE; KETONE; UNCLASSIFIED DRUG;

EID: 3042582144     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.111     Document Type: Article
Times cited : (35)

References (16)
  • 1
    • 0342757538 scopus 로고    scopus 로고
    • For general methods of diphenyl ether formation see: (Review)
    • For general methods of diphenyl ether formation see: Sawyer J.S. Tetrahedron. 56:2000;5045. (Review)
    • (2000) Tetrahedron , vol.56 , pp. 5045
    • Sawyer, J.S.1
  • 3
    • 3042576584 scopus 로고    scopus 로고
    • note
    • 4: C, 65.37; H, 4.31; N, 5.44%. Found: C, 65.14; H, 4.07; N, 5.34%
  • 15
    • 3042625201 scopus 로고    scopus 로고
    • note
    • 4: C, 65.37; H, 4.31; N, 5.44%. Found: C, 65.11; H, 4.09; N, 5.39%
  • 16
    • 3042527757 scopus 로고    scopus 로고
    • note
    • All products analyzed correctly by microanalysis. Representative procedure: A mixture of 4-fluoronitrobenzene (0.5 mL, 4.7 mmol), 2′-hydroxyacetophenone (0.96 g, 7.1 mmol), and potassium carbonate (2.0 g, 14.0 mmol) in DMF (20 mL) was heated with stirring at 120°C for 2 h. The reaction mixture was poured into an ice water mixture and the resulting tan solid was collected by filtration and dried. The solid was triturated with ether/hexane to cleanly give 3 as a cream colored solid, 0.89 g (73%)


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