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Incremental Solvation Precedes Ion‐Pair Separation in Enantiomerization of a Cyano‐Stabilized Grignard Reagent
Author(s) -
Patwardhan Neeraj N.,
Gao Ming,
Carlier Paul R.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102253
Subject(s) - solvation , reagent , ion , chemistry , grignard reagent , organic chemistry
Concerted or stepwise? Ion‐pair separation is often proposed as a mechanism for enantiomerization of organolithium reagents in ethereal solvents. But what is the timing of the solvation and bond‐cleavage events? Are they concerted, or does one precede the other? Reaction order and Eyring studies of Grignard 1 in Et 2 O/toluene mixtures clearly demonstrate addition of solvent occurs before rupture of the MgC bond.