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Volumn , Issue 5, 2007, Pages 765-768

A novel catalytic hypervalent iodine oxidation of p-alkoxyphenols to p-quinones using 4-iodophenoxyacetic acid and Oxone®

Author keywords

4 iodophenoxyacetic acid; Catalysis; Hypervalent iodine oxidation; Oxone ; p alkoxyphenol; p quinone

Indexed keywords

1,4 BENZOQUINONE; 4 ALKOXYPHENOL DERIVATIVE; 4 BUTOXYPHENOL DERIVATIVE; 4 IODOPHENOXYACETIC ACID; 4 QUINOLONE DERIVATIVE; ACETONITRILE; IODINE; IODOBENZENE; PHENOL DERIVATIVE; PHENOXYACETIC ACID; SODIUM PEROXIDE; UNCLASSIFIED DRUG;

EID: 33947725132     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-970758     Document Type: Article
Times cited : (59)

References (49)
  • 1
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    • Patai, S, Rappoport, Z, Eds, John Wiley & Sons: Chichester
    • (a) The Chemistry of the Quinonoid Compounds, Part 1 and 2, Vol. 2; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1988.
    • (1988) The Chemistry of the Quinonoid Compounds, Part 1 and 2 , vol.2
  • 2
    • 0003868021 scopus 로고    scopus 로고
    • Thomson, R. H, Ed, Blackie Academic and Professional: London
    • (b) Naturally Occurring Quinones IV, Recent Advances; Thomson, R. H., Ed.; Blackie Academic and Professional: London, 1997.
    • (1997) Naturally Occurring Quinones IV, Recent Advances
  • 9
    • 0001213492 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
    • (1996) Chem. Rev , vol.96 , pp. 1123
    • Stang, P.J.1    Zhdankin, V.V.2
  • 12
    • 0003579937 scopus 로고    scopus 로고
    • Varvoglis, A, Ed, Academic Press: San Diego
    • (d) Hypervalent Iodine in Organic Synthesis; Varvoglis, A., Ed.; Academic Press: San Diego, 1997.
    • (1997) Hypervalent Iodine in Organic Synthesis
  • 18
    • 0035800351 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812.
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 2812
    • Wirth, T.1
  • 35
    • 0021206946 scopus 로고    scopus 로고
    • Compound 1a is commercially available. For preparation, see: Abraham, D. J.; Kennedy, P. E.; Mehanna, A. S.; Patwa, D. C.; Williums, F. L. J. Med. Chem. 1984, 27, 967.
    • Compound 1a is commercially available. For preparation, see: Abraham, D. J.; Kennedy, P. E.; Mehanna, A. S.; Patwa, D. C.; Williums, F. L. J. Med. Chem. 1984, 27, 967.
  • 37
    • 33746211332 scopus 로고    scopus 로고
    • 3 has been reported, see: Carreño, M. C.; González-López, M.; Urbano, A. Angew. Chem. Int. Ed. 2006, 45, 2737.
    • 3 has been reported, see: Carreño, M. C.; González-López, M.; Urbano, A. Angew. Chem. Int. Ed. 2006, 45, 2737.
  • 38
    • 3342981841 scopus 로고    scopus 로고
    • It is not clear whether iodine(V) species was formed during the reaction. However, many reports for the formation of iodine(V) species by the oxidation of iodoarene with oxidizing reagent have been reported, see: (a) Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901.
    • It is not clear whether iodine(V) species was formed during the reaction. However, many reports for the formation of iodine(V) species by the oxidation of iodoarene with oxidizing reagent have been reported, see: (a) Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901.
  • 47
    • 0000978251 scopus 로고    scopus 로고
    • For the oxidation of phenol derivatives with iodine(V) species, see ref. 3b and: Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Stobie, A. Tetrahedron Lett. 1982, 23, 957.
    • For the oxidation of phenol derivatives with iodine(V) species, see ref. 3b and: Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Stobie, A. Tetrahedron Lett. 1982, 23, 957.
  • 48
    • 33947724035 scopus 로고    scopus 로고
    • It is possible that iodine(III) species may be oxidized by Oxone® to regenerate iodine(V) species before the reaction of iodine(III) with phenol
    • It is possible that iodine(III) species may be oxidized by Oxone® to regenerate iodine(V) species before the reaction of iodine(III) with phenol.
  • 49
    • 33947714789 scopus 로고    scopus 로고
    • Typical Reaction Procedure: To a solution of 2 (1 mmol) in MeCN-H2O (2:1, 6 mL) was added 1a (0.2 mmol) followed by Oxone® (1 mmol) at r.t. and the resulting mixture was stirred at the same temperature. After 2 was completely consumed indicated by TLC, the mixture was diluted with EtOAc and washed with H2O. The organic layer was then washed with aq sat. NaHCO3 solution and dried, concentrated to give pure 3. If necessary, the product was purified by column chromatography on silica gel to give pure quinone. The alkaline solution was acidified by 10% HCl solution and extracted with EtOAc. The organic layer was washed with aq Na2S2O3 solution and dried, then concentrated to give recovered 1a which was purified by recrystallization from Et2O-hexane. All new compounds gave satisfactory spectroscopic data
    • 2O-hexane. All new compounds gave satisfactory spectroscopic data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.