title: Friedel-Craft acylation of ar-himachalene: synthesis of acyl-ar-himachalene and a new acyl-hydroperoxide.
abstract: Friedel-Craft acylation at 100 °C of 2,5,9,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene [ar-himachalene], a sesquiterpenic hydrocarbon obtained by catalytic dehydrogenation of α-, β- and γ-himachalenes, produces a mixture of two compounds: (3,5,5,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)-ethanone (2, in 69% yield), with a conserved reactant backbone, and 3, with a different skeleton, in 21% yield. The crystal structure of 3 reveals it to be 1-(8-ethyl-8-hydroperoxy-3,5,5-trimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-ethanone. In this compound O-H…O bonds form dimers. These hydrogen-bonds, in conjunction with weaker C-H…O interactions, form a more extended supramolecular arrangement in the crystal.
authors.affiliation: Laboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia BP 2390, Marrakech 40001, Morocco.
authors.forename: Issam
authors.initials: I
authors.lastname: Hossini
authors.forename: Mohamed Anoir
authors.initials: MA
authors.lastname: Harrad
authors.forename: Mustapha
authors.initials: M
authors.lastname: Ait Ali
authors.forename: Larbi
authors.initials: L
authors.lastname: El Firdoussi
authors.forename: Abdallah
authors.initials: A
authors.lastname: Karim
authors.forename: Pedro
authors.initials: P
authors.lastname: Valerga
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Puerta
mesh_terms: D000215:Acylation; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D006861:Hydrogen Peroxide / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D012717:Sesquiterpenes; D006861:Hydrogen Peroxide; C412292:himachalene