Aromatisation in adducts of alpha-terpinene: Influence of hindered internal rotations

Abstract

Each adduct of alpha-terpinene with p-quinone and 1,4-naphthoquinone in Ac(2)O/Et(3)N at 180 C gives two aromatic products, one of which had a distinctive smell formed by the loss of an ethylene group. Here, we report the crystal structure of (1RS, 4RS)-1-isopropyl-4-methyl-1,4-dihydro-1,4-ethanoanthracene-9,10-diyl diacetate. It is crystallised in an orthorhombic space group, Pbca, with cell dimensions a = 10.2899(7), b = 19.7804(9), c = 19.7519(8) angstrom and Z = 8. According to its NMR and X-ray diffraction data, the isopropyl and acetate groups slowly rotate.