19158-70-4Relevant academic research and scientific papers
REACTION OF ALDEHYDES AND KETONES WITH t-BUTYL BROMIDE-DIMETHYL SULPHOXIDE
Armani, E.,Dossena, A.,Marchelli, R.,Casnati, G.
, p. 2035 - 2040 (2007/10/02)
Reacting aldehydes and ketones with the "ButBr-Me2SO" system produces the corresponding α-bromoderivatives 2.In the case of ketones, where more than one regioisomer is possible, bromination is obtained exclusively at the more highly substituted α-position.With slight modifications of the reaction conditions (addition of Me2S, Me2SO) it is possible to obtain "in situ" formation of either dimethyl(2-oxo-phenylalkyl)sulphonium salts 3 or of α-methylthioderivatives 4.Dimethyl(1-methyl-2-oxo-2-phenylethyl)sulphonium bromide (3h) during crystallization undergoes spontaneous resolution of the two enantiomers, as demonstrated by single crystal X-ray analysis and absolute configuration assignment.
Synthesis and Spontaneous Resolution by Crystallization of R,S-(+/-)-Dimethyl(1-methyl-2-oxo-2-phenylethyl)sulphonium Bromide. X-Ray Structure and Absolute Configuration of the R-Enantiomer
Dossena, Arnaldo,Marchelli, Rosangela,Armani, Elisabetta,Fava, Giovanna Gasparri,Belicchi, Marisa Ferrari
, p. 1196 - 1197 (2007/10/02)
R,S-(+/-)-Dimethyl(1-methyl-2-oxo-2-phenylethyl)sulphonium bromide (3a), obtained from 1-phenylpropanone by bromination with t-butyl bromide-dimethyl sulphoxide and further reaction with dimethyl sulphide, undergoes spontaneous resolution of its two enantiomers upon crystallization, as demonstrated by a single crystal X-ray analysis and assignment of absolute configuration (R).
