Ring tension, hydrocarbon acidity, and new super-bases

Addn. of di-Na pinacolate or KOCMe3 increased the transmetalating power of pentylsodium in alkane solvents. Some hydrocarbons thus metalated were Me3CCH:CH2, camphene, bicyclo[2.2.2]octene, spiro[4.4]nona-1,3-diene, nortricyclane, norcarane, and housane. Cyclobutanes remained inert.