Reactions of <i>exo-exo</i>-hexacyclo[9.2.1.0^2,10.0^3,8.0^4,6.0^5,9]tetradecane with Aliphatic Alcohols under the Action of Ionic Liquids

Abstract

It has been established for the first time that ionic liquids catalyze the alcoholysis of a hydrogenated norbornadiene dimer—exo-exo-hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradecane with aliphatic C1-C4 alcohols. The reaction proceeds along the hydrocarbon cyclopropane ring by a regioselective C4-C5 bond cleavage to form the previously undescribed 4-exo-alkoxypentacyclo[8.2.1.15,8.02,9.03,7]tetradecanes in high yields, which is promising as a precursor for the synthesis of drugs, as well as in the role of transmission media.

Keywords

• alcoholysis
• norborndiene dimer
• alcohols
• ionic liquids