Synthesis and Mechanistic DFT Studies of Arylhimachalene via Bromination of Himachalenes

A. Faris; I. Louchachha; Y. Edder; A.A. Mansour; B. Boualy; R. Salghi; A. Karim

doi:10.2174/0115701786337235241110172515

ISSN: 1570-1786
E-ISSN: 1875-6255

Synthesis and Mechanistic DFT Studies of Arylhimachalene via Bromination of Himachalenes
Authors: A. Faris¹, I. Louchachha¹, Y. Edder^1,2, A.A. Mansour³, B. Boualy⁴, R. Salghi^3,5 and A. Karim¹
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¹ Coordination Chemistry and Catalysis Team, Department of Chemistry, Faculty of Sciences Semlalia, Cadi Ayyad University, BP 2390, Marrakech 40001, Morocco ; ² Department of Chemistry, Faculty of Science, Choaib Doukkali University, B.P. 299, El Jadida 24000, Morocco; ³ Laboratory of Applied Chemistry and Environment, ENSA, University Ibn Zohr, P.O. Box 1136, Agadir 80000, Morocco ; ⁴ Environmental Sciences and Applied Materials Research Team, Multidisciplinary Research and Innovation Laboratory, Polydisciplinary Faculty of Khouribga, Sultan Moulay Slimane University of Beni Mellal, B.P: 145- 25000, Khouribga, Morocco ; ⁵ Euromed Research Center, Euromed Polytechnic School, Euromed University of Fes, Eco-Campus, Fes-Meknes Road, 30030 Fes, Morocco
Source: Letters in Organic Chemistry, Volume 22, Issue 5, May 2025, p. 343 - 347
DOI: https://doi.org/10.2174/0115701786337235241110172515
- Received: 07 Jul 2024
- Accepted: 18 Sep 2024
- Available online: 01 Jan 2025

Abstract

Background

Arylhimachalene is a sought-after natural sesquiterpene, found in small quantities in the essential oil of Atlas cedar (Cedrus atlantica). Herein, we present a simple and efficient method for synthesizing this molecule, involving the bromination of a mixture of himachalene (the principal constituent of the same oil) and a mechanistic study based on density functional theory (DFT) calculations.

Methods

The synthesis of arylhimachalene was carried out by bromination using Br2/CH2Cl2. The resulting product was isolated by silica gel column chromatography and characterized by NMR spectroscopy.

Results

The treatment of the himachalene mixture with bromine led to the formation of arylhimachalene, as well as other rearrangement products catalyzed by in situ-formed bromic acid.

Conclusion

This study highlights the development of a simple method for synthesizing a natural molecule of interest, serving as a basis for numerous scientific studies, and also includes a mechanistic study of this synthesis.

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Synthesis and Mechanistic DFT Studies of Arylhimachalene via Bromination of Himachalenes

Lett. Org. Chem. 22, 343 (2025); https://doi.org/10.2174/0115701786337235241110172515

/content/journals/loc/10.2174/0115701786337235241110172515

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Supplementary material is available on the publisher’s website along with the published article.

Article Type: Letter

Keyword(s): aromatization; arylhimachalene; atlas cedarwood oil; bromination; DFT calculations; Himachalene

Synthesis and Mechanistic DFT Studies of Arylhimachalene via Bromination of Himachalenes

Abstract

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Supplementary material is available on the publisher’s website along with the published article.

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