Formation of meta-Arylsulfanyl- and meta-(Alkylsulfanyl)phenols from Cyclohexane-1,3-diones
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Do Van Thanh, N., Patra, S., & Clive, D. L. J. (2018). Formation of meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols from cyclohexane-1,3-diones. Tetrahedron, 74(32), 4343–4350. https://doi-org.login.ezproxy.library.ualberta.ca/10.1016/j.tet.2018.06.059
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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.
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http://purl.org/coar/resource_type/c_6501 http://purl.org/coar/version/c_b1a7d7d4d402bcce http://purl.org/coar/version/c_71e4c1898caa6e32
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en