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Volumn 34, Issue 3, 1993, Pages 545-548

Oxidations of substituted phenols with hypervalent iodine : Applications to the phthalide annulation route to anthraquinones

Author keywords

anthraquinones; Oxidation; phthalide anions; quinone monoacetals

Indexed keywords

ANTHRAQUINONE DERIVATIVE;

EID: 0027454804     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(93)85123-E     Document Type: Article
Times cited : (58)

References (29)
  • 11
    • 33751029353 scopus 로고
    • The Diels–Alder reaction of 4-methoxy-7-hydroxyisobenzofuran with methyl vinyl ketone; a general method for identification of some regioisomeric α-naphthols
    • (1985) Canadian Journal of Chemistry , vol.63 , pp. 735-738
    • Keay1    Rodrigo2
  • 19
    • 84918717645 scopus 로고    scopus 로고
    • 4. The products were used without further purification in the subsequent annulation reactions. Only in the cases of (6d), (6e) and (9c) were the oxidation products purified by chromatography.
  • 20
    • 84918717560 scopus 로고    scopus 로고
    • All crystalline compounds gave satisfactory nmr, ir and mass spectra as well as combustion analyses. Non-crystalline dienones were identified by nmr prior to annulation.
  • 21
    • 84918713894 scopus 로고    scopus 로고
    • 11d; (13a), 23/220–221.5; (13b), 48/159–60:%Yield of anthraquinone based on purified dienone, m.p.°C: (7d), 88/206-7; (10c), 84/160–163.
  • 26
    • 84918737543 scopus 로고    scopus 로고
    • 1H-nmr spectrum of the product which shows a resonance (δ 13 ppm) indicative of a single hydrogen bonded phenolic proton.
  • 27
    • 84918754498 scopus 로고    scopus 로고
    • 14.
  • 29
    • 84918718807 scopus 로고    scopus 로고
    • 1H nmr shift of the proton β to the carbonyl. In the case of 2,4-dienones, this resonance occurs close to δ 6.0 ppm, whereas in the isomeric structure it occurs at a lower field closer to δ 6.4 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.