Organosamariums from Reaction of Alkyl Halides with Samarium(II) Derivatives

J. L. Namy; J. Collin; C. Bied; H. B. Kagan

doi:10.1055/s-1992-21472

Synlett 1992; 1992(9): 733-734
DOI: 10.1055/s-1992-21472

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Organosamariums from Reaction of Alkyl Halides with Samarium(II) Derivatives

J. L. Namy^* , J. Collin, C. Bied, H. B. Kagan

^*Laboratoire de Synthèse Asymétrique (URA CNRS 1497), Institut de Chimie Moléculaire d'Orsay, Université Paris-Sud, F-91405 Orsay, France

Abstract

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Bis(cyclopentadienyl)samarium (SmCp₂) and alkyl halides gave organosamariums stable at -10 °C and reactive towards electrophiles. Samariuim(II) iodide did not give stable alkylsamariums. However internal quenching with ethan[²H]ol provided high yields of the monodeuterated alkane. In the latter case, an unstable organosamarium species was formed which needed an in situ trapping agent. The samarium analogue of the Barbier reaction is discussed in the light of these results. Some additional Barbier experiments were performed in the presence of samarium(II) iodide in tetrahydrofuran. It is concluded that under standard conditions (in the absence or presence of hexamethylphosphoramide) an unstable and reactive organosamarium species is formed which is immediately trapped by the carbonyl compound.

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