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A Family of Routes to Substituted Phenols, Including Meta-Substituted Phenols

  • Author(s) / Creator(s)
  • A new family of routes to substituted phenols has been developed. 2-Bromo-3-
    methoxycyclohex-2-en-1-ones are readily deprotonated at C-6 and the resulting anions react
    smoothly with a variety of electrophiles; treatment with DBU in PhMe at room temperature then
    results in efficient aromatization to benzene derivatives of regiochemically defined substitution
    pattern. This sequence affords phenolic azides (ArN3), sulfides (ArSR, ArSAr'), selenides
    (ArSePh), alcohols [ArCH(OH)R], amino derivatives [ArCH(NHSO2Ar')R), and 1,2-
    benzenediols. A complementary set of substitution patterns is obtained by DIBAL-H reduction
    or reaction with a Grignard reagent before aromatization; the latter process gives compounds in
    which the newly-introduced substituent is meta to the phenolic hydroxyl.

  • Date created
    2015-01-01
  • Subjects / Keywords
  • Type of Item
    Article (Draft / Submitted)
  • DOI
    https://doi.org/10.7939/r3-fbvm-7z62
  • License
    Attribution-NonCommercial 4.0 International
  • Language
  • Citation for previous publication
    • Shao, W., & Clive, D. L. J. (2015). A Family of Routes to Substituted Phenols, Including Meta-Substituted Phenols. Journal of Organic Chemistry, 80(24), 12280–12287. https://doi-org.login.ezproxy.library.ualberta.ca/10.1021/acs.joc.5b02187