73975-42-5Relevant academic research and scientific papers
Regioselective ruthenium catalysed H-D exchange using D2O as the deuterium source
Piola, Lorenzo,Ferandez-Salas, Jos A.,Manzini, Simone,Nolan, Steven P.
supporting information, p. 8683 - 8688 (2014/12/10)
An efficient and convenient ruthenium catalysed method for a regiospecific H/D exchange using D2O is described. Organic moieties such as pyridine, oxazole, imidazole, pyrazole, ester, ketone and carboxylic acid have been found effective directing groups in this transformation. In addition, the deuteration of the enantiopure (S)-Ketoprofen leads to the incorporation of three deuterium atoms with retention of molecular chirality.
LIGAND COUPLING AND PSEUDOROTATION IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENTS
Oae, Shigeru,Takeda, Takashi,Kawai, Tsutomu,Furukawa, Naomichi
, p. 133 - 138 (2007/10/02)
In the reaction of benzyl 2-pyridyl sulfoxide (1) with C6H5CH2MgCl, the incoming Grignard reagent tends to couple preferentially with 2-pyridyl group at lower temperatures, whereas, at higher temperatures, coupling between benzyl and 2-pyridyl groups with 1 tends to increase due presumably to the relatively more facile pseudorotation at higher temperatures.
A New Acid-catalysed Rearrangement of Thiosulphinates to α-Acetylthio-sulphoxides in Acetic Anhydride
Furukawa, Naomichi,Morishita, Tsuyoshi,Akasaka, Takeshi,Oae, Shigeru
, p. 432 - 440 (2007/10/02)
Some thiosulphinates with at least one proton on the carbon adjacent to the sulphenyl sulphur react with acetic anhydride containing acetic acid to afford the corresponding α-acetylthio-sulphoxides.The mechanism of this reaction was studied using thiosulphinates labelled with (2)H, (13)C, and (18)O.These tracer experiments demonstrated that the reaction proceeds via an initial Ei reaction to form the corresponding sulphenic acid ant thioaldehyde followed by recombination in which the sulphur atom of the sulphenic acid adds to the carbon atom of the thioaldehyde, eventually affording the rearranged α-acetylthio-sulphoxide.The formation of the sulphenic acid was confirmed by trapping it with methyl acrylate.The mechanism of the reaction is discussed.
