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Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide
Laboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia BP 2390, Marrakech 40001, Morocco
Departamento de CMIM y Química Inorgánica, Facultad de Ciencias, Universidad de Cadiz, Campus Universitario Río San Pedro, Puerto Real 11510, Spain
* Author to whom correspondence should be addressed.
Received: 19 May 2011; in revised form: 29 June 2011 / Accepted: 8 July 2011 / Published: 14 July 2011
Abstract: Friedel-Craft acylation at 100 °C of 2,5,9,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene [ar-himachalene (1)], 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.
Keywords: ar-himachalene; Friedel-Craft acylation; hydroperoxyde; hydrogen-bonds
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MDPI and ACS Style
Hossini, I.; Harrad, M.A.; Ait Ali, M.; El Firdoussi, L.; Karim, A.; Valerga, P.; Puerta, M.C. Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide. Molecules 2011, 16, 5886-5895.
Hossini I, Harrad MA, Ait Ali M, El Firdoussi L, Karim A, Valerga P, Puerta MC. Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide. Molecules. 2011; 16(7):5886-5895.
Hossini, Issam; Harrad, Mohamed Anoir; Ait Ali, Mustapha; El Firdoussi, Larbi; Karim, Abdallah; Valerga, Pedro; Puerta, M. Carmen. 2011. "Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide." Molecules 16, no. 7: 5886-5895.