81572-06-7Relevant academic research and scientific papers
Preparation of Chiral 1-Deuteriobenzenemethanethiols by Using α',β Elimination of Carbanions Derived from Benzylic Thioethers
Biellmann, Jean-Francois,d'Orchymont, Hugues
, p. 2882 - 2886 (1982)
The α',β elimination of the carbanion derived from benzyl isolongifolyl thioether and benzyl camphyl thioether gives the chiral benzyl mercaptan, the S isomer with 38 +/- 6percent ee and the R isomer with 49 +/- 7percent ee.The chirality of the benzyl mercaptan was determined by optical rotation of benzyl methyl thioether and thiosulfone.The enantiomeric excess was evaluated from 1H NMR measurement of ethyl (benzylthio)phenylacetate prepared from (-)-mandelic acid.The enantiomeric excess at carbon C-2 of ethyl (benzylthio)phenylacetate wasdetermined with the chiral europium chelate and was about 60percent.These results are discussed with reference to the transition state of the α,β elimination and to related processes.
