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Volumn 69, Issue 6, 2004, Pages 2224-2227

Electrophilic Amination of 4-Fluorophenol with Diazenes: A Complete Removal of the Fluorine Atom

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; FLUORINE; ZIRCONIUM COMPOUNDS;

EID: 12144286274     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035856b     Document Type: Article
Times cited : (18)

References (78)
  • 54
    • 0002422951 scopus 로고    scopus 로고
    • Attanasi, O. A., Spinelli D., Eds.; Società Chimica Italiana: Rome
    • (d) Polanc, S. In Targets in Heterocyclic Systems. Chemistry and Properties; Attanasi, O. A., Spinelli D., Eds.; Società Chimica Italiana: Rome, 2000; Vol. 3 (1999), pp 33-91.
    • (2000) Targets in Heterocyclic Systems. Chemistry and Properties , vol.3 , Issue.1999 , pp. 33-91
    • Polanc, S.1
  • 73
    • 1642327961 scopus 로고    scopus 로고
    • Reference 3b, p 681
    • Reference 3b, p 681.
  • 75
    • 1642282416 scopus 로고    scopus 로고
    • note
    • The reaction yields of 4-fluorophenol with dialkyl diazenedi-carboxylates 1-3 are lower than those of 2-chlorophenol with the same diazenes. In the case of 2-chlorophenol, the reactions are typical electrophilic aromatic substitutions while 4-fluorophenol fluorophenol follows the reaction pathway proposed in Scheme 4. After radial chromatography of the reaction mixtures, obtained from 4-fluorophenol and dialkyl diazenedicarboxylates, a certain amount of an unidentified dark residue (tar) remains at the baseline (sample line) of the silica gel plate. This is the reason for lower yields of products 9-11 (Table 2, entries 1-3), prepared from 4-fluorophenol, compared to the yields of the same products that were synthesized from 2-chlorophenol (Table 2, entries 5-7).
  • 78
    • 1642295338 scopus 로고    scopus 로고
    • note
    • 3F) takes place.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.