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Formation of meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols from cyclohexane-1,3-diones

Author:
Do Van Thanh, Nhan, Patra, Subrata, Clive, Derrick L.J.
Source:
Tetrahedron 2018 v.74 no.32 pp. 4343-4350
ISSN:
0040-4020
Subject:
acetonitrile, ambient temperature, aromatization, bromination, chemical structure, phenols, potassium carbonate, thiols
Abstract:
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 3-(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.
Agid:
6097609