Addition of n-butyllithium to an aldimine: role of chelation, aggregation, and cooperative solvation.

نویسندگان

  • Bo Qu
  • David B Collum
چکیده

Rate studies of the addition of n-BuLi in the presence of TMEDA to potentially chelating aldimines are consistent with a combination of monomer- and dimer-based mechanisms. Using mixtures of TMEDA and Et2O reveals cooperative solvation in which both Et2O and TMEDA coordinate to lithium at the monomer- and dimer-based transition structures. The four discrete mechanisms are affiliated with markedly different stereochemistries of the 1,2-addition.

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عنوان ژورنال:
  • Journal of the American Chemical Society

دوره 127 31  شماره 

صفحات  -

تاریخ انتشار 2005