Chemical Transformations of Tetracyclo[3.3.1.13,7.01,3]decane (1,3-Dehydroadamantane): VII. Reaction of 1,3-Dehydroadamantane with Alkanediols and Amino Alcohols

Abstract

The reaction of 1,3-dehydroadamantane with C₂–C₆ α,ω-alkanediols selectively afforded ω-(adamantan- 1-yloxy)alkan-1-ols in 87–94% yield. The reaction of 1,3-dehydroadamantane with ω-aminoalkan-1- ols (2-aminoethanol and 3-aminopropan-1-ol) gave mixtures of addition products through the oxygen and nitrogen atoms, which can be readily separated by fractional vacuum distillation or crystallization.