Formation of meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols from cyclohexane-1,3-diones
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.
Do Van Thanh, Nhan,Patra, Subrata,Clive, Derrick L.J.
Facile Deoxygenation of Phenols and Enols Using Sodium Borohydride-Nickel Chloride
A facile deoxygenation reaction of phenol and 1,3-dicarbonyl compounds was investigated.Phenols, enolizable 1,3-diketones and 3-ketoesters were converted into the toluene-p-sulfonates which were reduced by a sodium borohydride-nickel chloride system to give the deoxygenated aromatic compounds, alcohols and esters, respectively.
Wang, Feng,Chiba, Kazuhiro,Tada, Masahiro
p. 1897 - 1900
(2007/10/02)
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