According to this:
https://owl.oit.umass.edu/departments/OrganicChemistry/appen...
toluene is slightly (by 1 point) less acidic than diisopropylamine in water (although the pKa is theoretical), but it is also less volatile. It might
be possible to make benzylsodium from sodium diisopropylamide, or failing this, to make e.g. naphthylmethylsodium the same way. Possibly in some
ethereal solvents or in toluene itself we might find that toluene is more acidic than diisopropylamine, which would be convenient.
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