Compounds of the type ZP(RNCH2CH2)(3)N where Z = a lone pair are proving to
be versatile reagents and catalysts for an ever increasing number of organ
ic transformations. These properties stem from the extraordinary basicity a
nd low nucleophilicity of the phosphorus atom when certain Z substituents i
nduce the bridgehead nitrogen to transannulate (even partially) to the phos
phorus. When Z = O, the phosphoryl oxygen also displays unusual basicity wh
en transannulation is caused.