Addition of disodium pinacolate or, particularly, potassium tert-butoxide considerably increases the transmetalating power of pentylsodium. A hexane slurry of such «NACNAOR» or «NACKOR» reagent mixtures readily and selectively converts 3,3-dimenthyl-1-butene, camphene, bicyclo[2.2.2]oct-2-ene, and spiro[4.4]nona-1,3-diene into sodio derivatives. The metalation of cyclopropanes such as nortricyclane, norcarane or bicyclo[2.1.0]pentane («housane») proved to be possible too, although the yields were less satisfactory. On the other hand, cyclobutanes were found to be virtually inert towards alcoholate-activated pentylsodium.
