Steric Effects in the Synthesis of 1,7-Dialkylindans

Article abstract of DOI:10.1021/jo00359a005

Synthesis routes to 1-alkyl(CH3,C2H5,i-C3H7)-6-methylindans and 1-alkyl(CH3,C2H5,i-C3H7)-7-methylindans are described.Members of the latter series, especially 1-isopropyl-7-methylindan, are sterically hindered through a peri interaction.This effect manifests itself throughout the study and necessitated use of alternative synthesis routes.Yields in the Grignard, Peterson olefination, Reformatsky, and Wittig reactions as well as catalytic hydrogenation and Li/NH3 reduction of α,β-unsaturated acids were compared.