Alkenylation of Adamantanols with Alcohols in the Presence of Sulfuric Acid

A series of adamantyl-containing alkenes were synthesized by the alkenylation of adamantan-1-ol with secondary alcohols in the presence of sulfuric acid. The scope of application of this reaction was explored to show that the alkenylation reaction with symmetrical dialkylcarbinols occurs in a selective fashion. The alkenylation of adamantan-1-ol with sec-pentanol and its higher homologs gives a mixture of isomeric alkenes. The reactions of substituted adamantanols with isopropanol, butan-2-ol, and cyclohexanol in the presence of sulfuric acid were studied, and a series of new unsaturated derivatives of the adamantane series were obtained.