32368-16-4Relevant academic research and scientific papers
Chemical oxidation studies of β-hydroxysulfides with tris(4-bromophenyl)aminium hexachloroantimonate: Diastereoselective sulfoxide obtaining and pinacol-type rearrangement
Donnici, Claudio Luis,Guimaraes, Sibele,De Melo, Angelita Cristine
, p. 1489 - 1497 (2007/10/03)
The chemical oxidation of some β-hydroxy-sulfides in the presence of tris(4-bromo-phenyl)aminium hexachloroantimonate (TBPA) is reported. The oxidation of 2-ethylsulfanyl-cyclohexan-1-ol (cis- and trans-) resulted the corresponding sulfoxides with good diastereoselectivity (d.e. 50%) and for 2-methyl-2-ethylsulfanyl-cyclohexan-1-ol and 2-ethylsulfanyl-1,2-diphenyl-ethanol, the corresponding nonsulfanylated ketones (61-75%) and ethyl ethanethiolsulfonate (51-65%) were obtained via oxidative cleavage and pinacol-type rearrangement.
REACTION OF Α-CHLORO KETONES WITH THIOLS
Mursakulov, I. G.,Ramazanov, E. A.,Kerimov, F. F.,Abbasov, I. M.,Zefirov, N. S.
, p. 1416 - 1425 (2007/10/02)
The reaction of α-chloro ketones with ethane-, propane-, and butanethiols leads to the corresponding (alkylthio)alkenes.Noncyclic chloro ketones give a mixture of the cis and trans isomers of di(alkylthio)alkenes, while the reaction of α-chloropinacoline leads only to the cis isomers of the 1,2-di(alkylthio)-3,3-dimethyl-1-butene.The mechanism of the reaction of α-chloro ketones with thiols includes nucleophilic substitution of the chlorine with the formation of alkylthio ketones.The addition of a further molecule leads to the corresponding intermediate alkylthio a cohols, which are easily dehydrated to the final products under the acidic conditions.
