Synthesis of 4-tert-Butyl-1,1-dimethylindan and 7-tert-Butyl-3,3-dimethyl-1-indanone and a Comparison of Isomers

Article abstract of DOI:10.1021/jo00341a032

4-tert-Butyl-1,1-dimethylindan was synthesized to help establish the identity of products (5- and 6-tert-butyl-1,1-dimethylindan as minor and major products, respectively) from the sulfuric acid catalyzed condensation of tert-butylbenzene and isoprene.NMR (1H and 13C) studies of these hydrocarbons and their corresponding indanones, obtained through chromic acid oxidation, provided structural proof.Gated decoupling experiments were crucial to complete assignment.