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Volumn 55, Issue 18, 1990, Pages 5287-5291

An Efficient and Selective Method for the Preparation of Iodophenols

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EID: 2642697712     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00305a026     Document Type: Article
Times cited : (176)

References (52)
  • 19
    • 85083010444 scopus 로고
    • An excellent review of methods for iodination of aromatic compounds has recently appeared
    • An excellent review of methods for iodination of aromatic compounds has recently appeared: Merkushev, E. B.; Synthesis 1988, 923.
    • (1988) Synthesis , pp. 923
    • Merkushev, E.B.1
  • 34
    • 85022726651 scopus 로고
    • There is one example in the literature in which a KI/KOC1 combination was used to iodinate 8-hydroxy-5-sulfoquxnoline to the corresponding 7-iodo compound: Claus, A. Arch. Pharm. 1893, 231, 704. Biochemists have used the combination of bleach and sodium iodide to achieve polyiodination of aromatic amino acids in proteins, but have not investigated the selectivity of the reaction
    • There is one example in the literature in which a KI/KOC1 combination was used to iodinate 8-hydroxy-5-sulfoquxnoline to the corresponding 7-iodo compound: Claus, A. Arch. Pharm. 1893, 231, 704. Biochemists have used the combination of bleach and sodium iodide to achieve polyiodination of aromatic amino acids in proteins, but have not investigated the selectivity of the reaction: Redshaw, M. R.; Lynch, S. S. J. Endocrinology 1974, 60, 527.
    • (1974) J. Endocrinology , vol.60 , Issue.527
    • Redshaw, M.R.1    Lynch, S.S.2
  • 35
    • 85022731515 scopus 로고
    • The use of alkyl hypoiodites in aromatic iodination has been described
    • The use of alkyl hypoiodites in aromatic iodination has been described: Glover, S. A.; Goosen, A.; Laue, H. A. H. J. S. Afr. Chem. Inst. 1973. 26. 77.
    • (1973) Afr. Chem. Inst. , vol.26 , Issue.77
    • Glover, S.A.1    Goosen, A.2    Laue, H. A. H. J. S.3
  • 37
    • 85022642164 scopus 로고    scopus 로고
    • where XA could be: IC1,I2, ClOH, etc. While we find the mechanism intriguing and are grateful to the referee for suggesting it, we do not feel that it explains adequately the variation in para/ortho ratio with the bulk of the R group in ROH solvent
    • where XA could be: IC1,I2, ClOH, etc. While we find the mechanism intriguing and are grateful to the referee for suggesting it, we do not feel that it explains adequately the variation in para/ortho ratio with the bulk of the R group in ROH solvent. The position of attack (ortho or para) of iodine ion on ii should be relatively independent of the bulk of R.
    • The position of attack (ortho or para) of iodine ion on ii should be relatively independent of the bulk of R
  • 45
    • 84943049716 scopus 로고
    • U.S. Patent, 2,131,258
    • Stoesser, W. C. U.S. Patent, 2,131,258; Chem. Abstr. 1938, 32, 9403.
    • (1938) Chem. Abstr. , vol.32 , pp. 9403
    • Stoesser, W.C.1


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