Improved synthesis of the chrysomelid pheromone (6R,7S)-(+)-himachala-9,11-diene via spontaneous bromination and didehydrobromination of 2,6,6,9-tetramethyl-bicyclo[5.4.0]undec-8-ene

Jimenez-Aleman, Guillermo Hugo; Schöner, Tim A.; Montero-Alejo, Ana L.; Brandt, Wolfgang; Boland, Wilhelm

doi:10.3998/ark.5550190.0013.326

Cited by 9 publications

(4 citation statements)

References 6 publications

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“…The reaction can be performed either on the mixture of three himachalenes or each taken separately (Scheme 18). Various dehydrogenating agents were used: selenium, 79,80 chloranil, 54 palladium, 81 Raney nickel, 82 bromine, 83 DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone). 84 The selectivity and yield of this transformation is dependent on the reagent employed and the operating conditions.…”

Section: Scheme 17 Synthesis Of (S)-ar-turmerone and Its Conversion Into (S)-ar-himachalene And (+)-Bisacumolmentioning

confidence: 99%

The chemistry of the himachalenes and atlantones from Cedrus

Oukhrib¹,

Zaki²,

Benharref³

2018

Arkivoc

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Synthesis and functionalization of natural products are useful procedures to access and develop new and interesting molecules with biological properties. In this review we discuss the major sesquiterpenes isolated from the essential oil of cedar, which represents a family of abundant and inexpensive natural materials. Some total synthesis and chemical transformations described in the literature have been included.

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Section: Scheme 17 Synthesis Of (S)-ar-turmerone and Its Conversion Into (S)-ar-himachalene And (+)-Bisacumolmentioning

confidence: 99%

The chemistry of the himachalenes and atlantones from Cedrus

Oukhrib¹,

Zaki²,

Benharref³

2018

Arkivoc

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“…Among the studied terpenes, dehydrogenation of himachalenes or dipentenes for the preparation of ar‐himachalene or p‐cymene are widely reported in the literature. [ 16 ] Regarding the dehydrogenation of himachalenes, different agents or catalysts were used for this reaction such as: lithium, [ 43 ] selenium, [ 44,45 ] chloranile, [ 46 ] Pd/C, [ 47 ] Raney nickel, [ 48 ] bromine, [ 49 ] DDQ, [ 50 ] and more recently palladium nanoparticles supported on mesoporous natural phosphate (Pd@NP) nanocatalysts. [ 15 ] In addition, the Pd@NP nanocatalysts were more efficient compared to the commercial heterogeneous catalysts (Pd/C and Raney nickel) as shown in Table S1.…”

Section: Introductionmentioning

confidence: 99%

Catalytic dehydrogenation of natural terpenes via CuPd alloy nanoparticles generated on mesoporous graphitic carbon nitride

Yalın

Sündü

Özer

et al. 2022

Applied Organom Chemis

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A facile wet‐chemical protocol for the synthesis of bimetallic CuPd alloy nanoparticles (NPs) anchored on mesoporous graphitic carbon nitride (m‐gCN), serving as both stabilizer and support material, was presented herein. The presented protocol allowed to synthesize nearly monodisperse CuPd alloy NPs with an average particle size of 3.9 ± 0.9 nm without use of any additional surfactants and to prepare CuPd/m‐gCN nanocatalysts with different Cu/Pd compositions (Cu25Pd75/m‐gCN, Cu35Pd65/m‐gCN, Cu16Pd74/m‐gCN, Cu32Pd68/m‐gCN, Cu10Pd90/m‐gCN, and Cu50Pd50/m‐gCN). After the detailed characterization of CuPd/m‐gCN nanocatalysts, they were utilized as catalysts in the dehydrogenation of terpenes. Among all tested nanocatalysts, Cu50Pd50/m‐gCN showed the highest activity in terms of the product yields within the same reaction time. Various parameters influencing the catalytic activity of Cu50Pd50/m‐gCN were studied using himachalene as a model substrate and the optimum conditions were determined. Under the optimized reaction conditions, the catalytic application of Cu50Pd50/m‐gCN nanocatalysts was extended to nine different terpenes and the corresponding products were obtained in high conversion yields (>90%) under mild conditions. A reusability test showed that Cu50Pd50/m‐gCN nanocatalysts can be re‐used up to four cycles without significant loss in their initial activity.

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“…[ 20,21 ] Due to its benefits, various studies have been reported on the synthesis of ar‐himachalene either by total synthesis or by dehydroaromatization of himachalene derivatives. [ 19–32 ] Different dehydroaromatization agents were used, such as: lithium, [ 29 ] selenium, [ 28,30 ] chloranile, [ 23 ] Pd/C, [ 20,24 ] Raney nickel, [ 31 ] bromine [ 32 ] or DDQ (2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone). [ 20 ]…”

Section: Introductionmentioning

confidence: 99%

“…[20,21] Due to its benefits, various studies have been reported on the synthesis of arhimachalene either by total synthesis or by dehydroaromatization of himachalene derivatives. [19][20][21][22][23][24][25][26][27][28][29][30][31][32] Different dehydroaromatization agents were used, such as: lithium, [29] selenium, [28,30] chloranile, [23] Pd/C, [20,24] Raney nickel, [31] bromine [32] or DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone). [20] It is noteworthy that different works are reported for the p-cymene preparation in the presence of various dipentene derivatives, such as carene, pinene or limonene.…”

Section: Introductionmentioning

confidence: 99%

Novel palladium nanoparticles supported on mesoporous natural phosphate: Catalytic ability for the preparation of aromatic hydrocarbons from natural terpenes

Mekkaoui

Aberkouks²,

Fkhar³

et al. 2020

Applied Organom Chemis

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Various ratios of palladium nanoparticles supported on mesoporous natural phosphate (Pd@NP) were prepared using the wetness impregnation method. The prepared catalysts were characterized by IR, XRD, CV, SEM, EDX, XRF, TEM and BET analysis. The reduction and preparation of the palladium nanoparticles afford a crystallite size of 10.88 nm. The performance of the synthesized catalyst was investigated in the solvent-free dehydroaromatization of α-, βand γ-himachalene mixture from Cedrus atlantica oil as a model substrate. In order to achieve an efficient and selective catalysis, the catalytic dehydroaromatization of various terpenes such as limonene, limonaketone, carvone, carveol and perillyl alcohol was studied. The Pd@NP catalyst performed a high catalytic activity, selectivity and recyclability in the terpenes dehydroaromatization reaction.

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Improved synthesis of the chrysomelid pheromone (6R,7S)-(+)-himachala-9,11-diene via spontaneous bromination and didehydrobromination of 2,6,6,9-tetramethyl-bicyclo[5.4.0]undec-8-ene

Cited by 9 publications

References 6 publications

The chemistry of the himachalenes and atlantones from Cedrus

The chemistry of the himachalenes and atlantones from Cedrus

Catalytic dehydrogenation of natural terpenes via CuPd alloy nanoparticles generated on mesoporous graphitic carbon nitride

Novel palladium nanoparticles supported on mesoporous natural phosphate: Catalytic ability for the preparation of aromatic hydrocarbons from natural terpenes

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