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Molecules 2011, 16(7), 5886-5895; doi:10.3390/molecules16075886
Article

Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide

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Received: 19 May 2011; in revised form: 29 June 2011 / Accepted: 8 July 2011 / Published: 14 July 2011
(This article belongs to the Section Organic Synthesis)
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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 ar-himachalene; Friedel-Craft acylation; hydroperoxyde; hydrogen-bonds
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

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.

Chicago/Turabian Style

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.



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