The photoinduced substitution reactions of halogenated alkanes (1-haloadamantanes, 1- haloronorbornanes, menthyl chloride) with a homologous series of amines or alcohols (methylamine, 2-methyl-2-aminopropane, methanol, or 2-methyl-2-propanol) to form the corresponding alkane-substituted amines or ethers and HCl were investigated. The geometry of the bridgehead carbons made SN2 reactions impossible. Nonpolar reaction ...