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Tetrahedron Letters
Volumn 31, Issue 22, 1990, Pages 3217-3220
A novel reaction of acetanilide with nitrobenzene in DMSO - an unusual solvent assisted regioselective aromatic nucleophilic substitution
Author keywords

[No Author keywords available]
Indexed keywords

AZOBENZENE; NITROSO DERIVATIVE;
EID: 0025368756     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)94736-1     Document Type: Article
Times cited : (16)
References (11)
  • 2
    • 84914378030 scopus 로고    scopus 로고
    • In a typical experiment, a mixture of acetanilide (0.05 mole), nitrobenzene (0.05 mole), sodium hydroxide (0.2 mole) and potassium carbonate (0.05 mole) in DMSO (75 ml) was heated at 80°C for 5 h. The reaction mixture was cooled to 28°C and drowned into ice-cold water (50 ml). It was then neutralized with dil. hydrochloric acid and extracted with ethyl acetate (5 x 50 ml). The dried extract was freed of the solvent and the residual liquid was chromatographed through a silica gel column using pet. ether: ethyl acetate (1:1) as eluant to isolate the products. Identical results were obtained when potassium carbonate was excluded from the mixture of bases. At 130°C, the reaction afforded a higher proportion of azobenzene (30%) with a decrease in formation of 3 (30%).
  • 3
    • 84914378029 scopus 로고
    • A standard sample of 3 was synthesized by the Fischer-Hepp rearrangement of N-nitroso diphenylamine as per the procedure described in
    • (1978) Japanese Patent 78,77,025
  • 7
    • 84914378026 scopus 로고    scopus 로고
    • neat = 7.68; Dδ = 0.2.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.