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Article Dans Une Revue Chinese Chemical Letters Année : 2020

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

Résumé

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 CC 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.
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hal-02613333 , version 1 (18-07-2022)

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Paternité - Pas d'utilisation commerciale

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Mustapha Ait El Had, Abdelouahd Oukhrib, Mohamed Zaki, Martine Urrutigoity, Ahmed Benharref, et al.. Versatile synthesis of cadalene and iso-cadalene from himachalene mixtures: Evidence and application of unprecedented rearrangements. Chinese Chemical Letters, 2020, 31 (7), pp.1851-1854. ⟨10.1016/j.cclet.2020.03.008⟩. ⟨hal-02613333⟩
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