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Volumn , Issue 5, 2003, Pages 723-725

Facile and efficient oxidative transformation of primary alcohols to methyl esters in water using hypervalent iodine(III) reagents

Author keywords

Alcohols; Esterification; Hypervalent iodine; Oxidations; Polymers

Indexed keywords

ALCOHOL DERIVATIVE; ESTER; IODINE; METHYL GROUP; POTASSIUM BROMIDE; REAGENT; WATER;

EID: 0037263591     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (64)

References (42)
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    • Top. Curr. Chem. 224; Springer-Verlag: Berlin, Heidelberg
    • Recent reviews see: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (b) Kita, Y.; Takada, T.; Tohma, H. Pure & Appl. Chem. 1996, 68, 627. (c) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997. (d) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409. (e) Ochiai, M. In Chemistry in Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999, Chap. 12. (f) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271. (g) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (h) Hypervalent Iodine Chemistry (Top. Curr. Chem. 224); Wirth, T., Ed.; Springer-Verlag: Berlin, Heidelberg, 2003.
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    • note
    • Among the typical hypervalent iodine(III or V) reagents, PhIO gave the best yield [75% yield], while other reagents such as phenyliodine diacetate (PIDA) [47% yield], phenyliodine bis(trifluoroacetate) (PIFA) [40% yield], Dess-Martin periodinane [trace], and o-iodoxybenzoic acid [trace], were also examined under the reaction conditions described in Table 1.
  • 24
    • 0033052277 scopus 로고    scopus 로고
    • Reviews see: (a) Drewry, D. H.; Coe, D. M.; Poon, S. Med. Res. Rev. 1999, 19, 97. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (c) Bhalay, G.; Dunstan, A.; Glen, A. Synlett 2000, 1846. (d) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650. (e) Togo, H.; Sakuratani, K. Synlett 2002, 1966.
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    • Drewry, D.H.1    Coe, D.M.2    Poon, S.3
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    • 0034533265 scopus 로고    scopus 로고
    • Reviews see: (a) Drewry, D. H.; Coe, D. M.; Poon, S. Med. Res. Rev. 1999, 19, 97. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (c) Bhalay, G.; Dunstan, A.; Glen, A. Synlett 2000, 1846. (d) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650. (e) Togo, H.; Sakuratani, K. Synlett 2002, 1966.
    • (2000) Synlett , pp. 1846
    • Bhalay, G.1    Dunstan, A.2    Glen, A.3
  • 27
    • 0035804384 scopus 로고    scopus 로고
    • Reviews see: (a) Drewry, D. H.; Coe, D. M.; Poon, S. Med. Res. Rev. 1999, 19, 97. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (c) Bhalay, G.; Dunstan, A.; Glen, A. Synlett 2000, 1846. (d) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650. (e) Togo, H.; Sakuratani, K. Synlett 2002, 1966.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 650
    • Kirschning, A.1    Monenschein, H.2    Wittenberg, R.3
  • 28
    • 0036458152 scopus 로고    scopus 로고
    • Reviews see: (a) Drewry, D. H.; Coe, D. M.; Poon, S. Med. Res. Rev. 1999, 19, 97. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (c) Bhalay, G.; Dunstan, A.; Glen, A. Synlett 2000, 1846. (d) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650. (e) Togo, H.; Sakuratani, K. Synlett 2002, 1966.
    • (2002) Synlett , pp. 1966
    • Togo, H.1    Sakuratani, K.2
  • 42
    • 0013157132 scopus 로고    scopus 로고
    • note
    • 2O, and the filtrate was dried and evaporated. The residue was purified by column chromatography to give pure 2.


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