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Volumn 66, Issue 11, 2008, Pages 1076-1084

Exploration and exploitation of synthetic use of oxoammonium ions in alcohol oxidation

Author keywords

[No Author keywords available]

Indexed keywords

IONS; KETONES; OXIDATION; TRANSITION METALS; UNSATURATED COMPOUNDS;

EID: 60249086098     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.66.1076     Document Type: Article
Times cited : (37)

References (89)
  • 2
    • 0000676907 scopus 로고
    • Trost, B. M, Fleming, I, Ley, S. V, Eds, Pergamon: Oxford
    • (a) Schlecht, M. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Ley, S. V., Eds.; Pergamon: Oxford, 1991; Vol 7, pp 251-327.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 251-327
    • Schlecht, M.F.1
  • 3
    • 13944255305 scopus 로고    scopus 로고
    • Bäckvall, J.-E, Ed; Willey-VCH. Weinheim, Germany
    • (b) Modern Oxidation Methods, Bäckvall, J.-E., Ed; Willey-VCH. Weinheim, Germany, 2004.
    • (2004) Modern Oxidation Methods
  • 37
    • 85036865592 scopus 로고    scopus 로고
    • Representative procedure for oxidation of alcohols under Anelli's conditions.6c To a stirring mixture of 3-phenyI propanol (200 mg, 1.47 mmol, 1-Me-AZADO (3, 0.244 mg, 1.47 μmol) in CH2Ch (3.9 ml) and aqueous sat. NaHCO3 (2 ml) containing KBr (17.5 mg, 0.074 M) and Bu4NBr (23.7 mg, 0.037 M) was added dropwise a premixed solution of aqueous NaOCl (8% Cl) and aqueous sat. NaHCO3 (3.3 ml, 1:1.4 v/v) at 0°C over 6 min. The mixture was vigorously stirred for 20 min at 0 °C, then quenched with aqueous sat. Na2S2O3 (4 ml, The aqueous layer was separated and extracted with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The residue was purified by flash column chromatography (SiO2, 1:6 Et2O:hexane) to give 3-phenylpropanal 177 mg, 1.32 mmol, 90, as a colorless oil
    • 2O:hexane) to give 3-phenylpropanal (177 mg, 1.32 mmol, 90%) as a colorless oil.
  • 38
    • 85036855540 scopus 로고    scopus 로고
    • Representative procedure for oxidation of alcohols under Margarita's conditions.6e PhI(OAc)2 (720 mg, 2.24 mmol) was added to a solution of cinnamyl alcohol (200 mg, 1.49 mmol) and 1-Me-AZADO (3, 2.47 mg, 14.9 μmol) in CH2Cl2 (1.5 ml, The reaction mixture was stirred for 40 min; it was then diluted with Et2O and quenched with aqueous sat. NaHCO3 (4 ml, followed by aqueous sat. Na 2S2O3 (4 ml, The layers were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The residue was purified by flash column chromatography (SiO2, 1:9 Et2O:hexane) to give cinnamaldehyde 183 mg, 1.39 mmol, 93, as a colorless oil
    • 2O:hexane) to give cinnamaldehyde (183 mg, 1.39 mmol, 93%) as a colorless oil.
  • 58
    • 85036893506 scopus 로고    scopus 로고
    • For a recent review on an oxochromium(VI)-based oxidant, see: (a) Luzzio, F. A. Org. React. 1998, 53, 1.
    • For a recent review on an oxochromium(VI)-based oxidant, see: (a) Luzzio, F. A. Org. React. 1998, 53, 1.
  • 77
    • 0032509230 scopus 로고    scopus 로고
    • Bobbitt, J, M. J. Org. Chem. 1998, 63, 9367.
    • (i) Bobbitt, J, M. J. Org. Chem. 1998, 63, 9367.
  • 89
    • 85036882251 scopus 로고    scopus 로고
    • If substrate possesses sufficiently acidic protons cf. allylic methine proton in cyclohexenol, the proton would be abstracted by the solvent to afford oxidized products
    • If substrate possesses sufficiently acidic protons (cf. allylic methine proton in cyclohexenol), the proton would be abstracted by the solvent to afford oxidized products.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.