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Synthesis 1987; 1987(7): 645-646
DOI: 10.1055/s-1987-28034
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Synthesis with Organoboranes;3.1 Allylic Monodeuteration of Olefins

Marek Zaidlewicz* , Chandra Sekhar Panda
  • *Institute of Chemistry, Nicolas Copernicus University, PL-87-100 Torun, Poland
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Publication Date:
20 August 2002 (online)

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Allylic diethylboranes are obtained from olefins via metalation with (trimethylsilylmethyl)potassium (generated in situ from bis(trimethylsilylmethyl)mercury and potassium sand) and subsequent reaction with chlorodiethylboron. The allylic boranes react with deuterium oxide to give isomerized olefins, monodeuterated in the allylic position.