Radical reactions on pinene-oxide derivatives induced by Ti(III)

Fernández-Mateos, A.; Teijón, P. Herrero; González, R. Rubio

doi:10.1016/j.tet.2011.10.004

Cited by 20 publications

(16 citation statements)

References 45 publications

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“…[ 24 ] Fernandez–Mateos was reported the titanocene chloride with granulated Zn power was dissolved in dry tetrahydrofuran (THF) for stirred at RT for 30 min, which gave them 89% yield of TC. [ 25 ] Rocha et al. reported the chemoselective isomerization of APO to TC using phosphotungstic acid (HPW) in the presence of DMA with 100% conversion and 90% selectivity of TC at 140 °C.…”

Section: Methodsmentioning

confidence: 99%

Sustainable Isomerization of α‐Pinene Oxide to trans‐Carveol using Formic Acid/Aniline System at Room Temperature

Ravi

Naikwadi

Biradar

2021

Advanced Sustainable Systems

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trans‐Carveol is an essential and expensive chemical used as valencia orange essence oil in the fragrance industry, and can be obtained through Brønsted acid‐catalyzed isomerization of α‐pinene oxide (APO) using hazardous solvent at higher temperatures. Therefore the development of a simple, metal‐free, and cost‐effective, sustainable method for isomerization of APO at milder conditions is desired. In this study, in situ formed formanilide (IFF) and tetrahydrofuran are used as active solvents and formic acid used as a Brønsted acid catalyst for selective isomerization of APO. Under the optimized conditions, the maximum 80% selectivity of trans‐carveol is achieved with complete APO conversion in 30 min at room temperature. The solvent system's practical utility is demonstrated at a 10 g scale with complete conversion and 76% selectivity at room temperature within 60 min. Furthermore, isotopic labeling experiments show donation of a proton from the IFF solvent.

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Section: Methodsmentioning

confidence: 99%

Sustainable Isomerization of α‐Pinene Oxide to trans‐Carveol using Formic Acid/Aniline System at Room Temperature

Ravi

Naikwadi

Biradar

2021

Advanced Sustainable Systems

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“…It has been shown that the deoxygenation occurs when operating in the absence of radical acceptors and that it depends on the substitution pattern [ 77 ]. On the basis of these observations, Fernández-Mateos and co-workers have recently reported the selective synthesis of terpenoids starting from pinene-oxide derivatives [ 78 ].…”

Section: Epoxide Reactions Mediated By Titanocenementioning

confidence: 99%

New Advances in Titanium-Mediated Free Radical Reactions

et al. 2012

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Titanium complexes have been widely used as catalysts for C-C bond-forming processes via free-radical routes. Herein we provide an overview of some of the most significant contributions in the field, that covers the last decade, emphasizing the key role played by titanium salts in the promotion of selective reactions aimed at the synthesis of multifunctional organic compounds, including nucleophilic radical additions to imines, pinacol and coupling reactions, ring opening of epoxides and living polymerization.

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“…4 Several essential products of the pharmaceutical and chemical industries can be manufactured utilizing the unique structure of α-pinene that is composed of a double bond and a strained four-membered ring, with both these moieties readily undergoing various transformations. [5][6][7][8][9][10] Thus, the conversion of α-pinene into high value-added chemical products is of commercial interest.…”

Section: Introductionmentioning

confidence: 99%

“…6,[10][11][12][13][14][15][16][17] The 2,3-epoxypinane (2) (Figure 2) often serves as a starting material for the synthesis of fragrances, flavors, and therapeutically active substances. 6 Verbenol (3) and verbenone (4) are nutritional supplements adding flavor and are important precursors in the production of fragrance chemicals. 10 Myrtenol (5) exhibits a range of biological activities and has been widely used in bactericidal, antiphlogistic, and fungicidal applications.…”

Section: Introductionmentioning

confidence: 99%

Selective aerobic allylic oxidation of α-pinene catalyzed by metalloporphyrins in the absence of solvents and additives

Dong

Wang

et al. 2019

Journal of Chemical Research

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Selective aerobic oxidation of α-pinene to high-value products is a major challenge in chemistry. Metalloporphyrins are proved to be selective catalysts for aerobic oxidation of simple hydrocarbons. Herein, we extend this method to more complex substrates using metallodeuteroporphyrins as model catalysts. It was found that the oxidation occurs mainly on the C=C and allylic C–H bonds of α-pinene influenced by the reaction temperature, reaction time, catalyst concentration, and oxygen flow rate. Allylic C–H oxidation products are obtained with a maximum selectivity value of 78.4% using the following reaction conditions: 105°C, 7 h, 5 ppm, and 60 mL/min. The influence of the metal nuclei of the metallodeuteroporphyrins on this reaction is also investigated. It was found that metallodeuteroporphyrins with Fe3+ as the metal nucleus exhibit the highest catalytic activity.

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Radical reactions on pinene-oxide derivatives induced by Ti(III)

Cited by 20 publications

References 45 publications

Sustainable Isomerization of α‐Pinene Oxide to trans‐Carveol using Formic Acid/Aniline System at Room Temperature

Sustainable Isomerization of α‐Pinene Oxide to trans‐Carveol using Formic Acid/Aniline System at Room Temperature

New Advances in Titanium-Mediated Free Radical Reactions

Selective aerobic allylic oxidation of α-pinene catalyzed by metalloporphyrins in the absence of solvents and additives

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