Citation: Ait El Had Mustapha, Oukhrib Abdelouahd, Zaki Mohamed, Urrutigoïty Martine, Benharref Ahmed, Chauvin Remi. Versatile synthesis of cadalene and iso-cadalene from himachalene mixtures: Evidence and application of unprecedented rearrangements[J]. Chinese Chemical Letters, ;2020, 31(7): 1851-1854. doi: 10.1016/j.cclet.2020.03.008 shu

Versatile synthesis of cadalene and iso-cadalene from himachalene mixtures: Evidence and application of unprecedented rearrangements

a.
Laboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité(URAC 16), Faculté des Sciences Semlalia, Université Cadi Ayyad, B. P. 2390, Marrakech, Morocco
b.
CNRS, LCC(Laboratoire de Chimie de Coordination), BP 44099, 31077, Toulouse Cedex 4, France
c.
INP-ENSIACET, 4 allée Emile Monso, 31030, Toulouse Cedex, France
d.
Université de Toulouse, UPS, ICT-FR 2599, 31062, Toulouse Cedex 9, France

^**

oukhrib@gmail.com

zaki.smc@gmail.com

chauvin@lcc-toulouse.fr

Received Date: 18 December 2019
Revised Date: 19 February 2020
Accepted Date: 3 March 2020
Available Online: 3 March 2020

Figures(3)

From a mixture of α-, β- and γ-himachalenes extracted from waste wood of Atlas cedar (Cedrus atlantica), cadalene (1, 6-dimethyl-4-isopropylnaphthalene) and iso-cadalene (1, 6-dimethyl-3-isopropylnaphthalene) were produced in two steps with up to 71%±5% yield through the ar-himachalene intermediate using I₂ and/or AlCl₃ as reagents. The selectivity is shown to sharply depend on the operating conditions: while I₂/AlCl₃ in dichloromethane promotes the formation of cadalene, the formation of iso-cadalene is favored in the presence of AlCl₃ in cyclohexane. The bicyclic aromatic compounds were thus obtained through unique rearrangements involving sequential C—C bond cleavage/formation and hydride transfer processes. In the absence of AlCl₃ or I₂, dihydrocurcumene was also found to be formed with up to 70% selectivity. A tentative mechanism is proposed and discussed.
- Aromatic reactivity,
- Cadalenes,
- Dihydrocurcumene,
- Himachalenes,
- Rearrangements
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1.
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