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

Kaya A. A., ŞENGÜL M., Menzek A., Kayaardi I., Karakus M., ŞAHİN E.

JOURNAL OF CHEMICAL RESEARCH, vol.35, no.9, pp.540-544, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 35 Issue: 9
  • Publication Date: 2011
  • Doi Number: 10.3184/174751911x13155890649111
  • Journal Name: JOURNAL OF CHEMICAL RESEARCH
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.540-544
  • Ondokuz Mayıs University Affiliated: No

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.