Sulfuric Acid → Homoadamantane

Participants

Reaction Steps

4-Homoisotwistane (II) is a compound disclosed by Krantz et al (Chem., Commun., 1971, 1287 and J. Amer. Chem. Soc., 95, 5662 (1973)) in their report concerning the selectivity of the intermolecular Diels-Alder reaction of 1-penten-5-ylcyclohexadienes. However, the selectivity of 4-homoisotwistane (II) is very low in this reaction and the starting 1-penten-5-ylcyclohexadiene is not readily available or cannot easily be synthesized. Accordingly, from the industrial viewpoint, it is very disadvantageous to synthesize 4-homoisotwistane according to the process of Krantz et al. Majerski et al (Tetrahedron Letters, 4915 (1973)) succeeded in synthesizing 4-homoisotwistane (II) in a yield of about 20 percent by reacting homoadamant-4-ene or homoadamantan-4-ol with concentrated sulfuric acid and n-pentane. This process also is industrially disadvantageous because it is difficult to obtain the starting homoadamantane derivatives.

Provenance & Evidence