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

Molecules

Issam Hossini¹  Mohamed Anoir Harrad¹  Mustapha Ait Ali¹  Larbi El Firdoussi¹  Abdallah Karim¹  Pedro Valerga¹ 

[1] ¹Laboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia BP 2390, Marrakech 40001, Morocco ²Departamento de CMIM y Química Inorgánica, Facultad de Ciencias, Universidad de Cadiz, Campus Universitario Río San Pedro, Puerto Real 11510, Spain

关键词: ar-himachalene;    Friedel-Craft acylation;    hydroperoxyde;    hydrogen-bonds;   

DOI  :  10.3390/molecules16075886

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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