Formation of meta-Arylsulfanyl- and meta-(Alkylsulfanyl)phenols from Cyclohexane-1,3-diones

• Author(s) / Creator(s)

  • Thanh, Nhan Do Van
  • Patra, Subrata
  • Clive, Derrick L. J.

• Reaction of cyclohexane-1,3-diones with TsCl/Et3N and treatment of the resulting 3-(tosyloxy)cyclohex-2-en-1-ones with aryl- or alkyl thiols and K2CO3 in MeCN gives 3-(arylsulfanyl)cyclohex-2-en-1-ones or (alkylsulfanyl)cyclohex-2-en-1-ones, respectively. These compounds are easily brominated at C-2 by using NBS in MeCN; exposure to DBU in MeCN at room temperature then causes aromatization to afford meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols.

• Date created

  2018-01-01

• Subjects / Keywords

  • meta-(arylsulfanyl)phenols
  • meta-(alkylsulfanyl)phenols
  • aromatization
  • bromination
  • sulfides

• Type of Item

  Article (Draft / Submitted)

• DOI

  https://doi.org/10.7939/r3-mnq6-qe91

• License

  Attribution-NonCommercial 4.0 International