RING OPENING OF EPOXIDES WITH CARBOXYLATES AND PHENOXIDES IN MICELLAR MEDIA CATALYZED WITH Ce(OTf)<sub>4</sub>

Iranpoor, Nasser; Firouzabadi, Habib; Safavi, Afsaneh; Shekarriz, Marzieh

doi:10.1081/scc-120005998

Cited by 21 publications

(9 citation statements)

References 38 publications

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“…Epoxides are versatile intermediates in organic synthesis, and their reactions with a variety of reagents such as electrophiles, nucleophiles, acids, bases, reducing agents, and some oxidizing agents are widely studied [7]. The reaction with nucleophiles such as oxygen compounds [8–10], nitrogen compounds (amine and derivatives of amines, azide, nitrate, and isocyanate), halides, and various carbon nucleophiles [11, 12] has been performed in both organic and aqueous solvents. …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Azidohydrin from Hura crepitans Seed Oil: A Renewable Resource for Oleochemical Industry and Sustainable Development

Adewuyi

Göpfert

Wolff

et al. 2012

ISRN Organic Chemistry

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The replacement of petrochemicals by oleochemical feedstocks in many industrial and domestic applications has resulted in an increase in demand for biobased products and as such recognizing and increasing the benefits of using renewable materials. In line with this, the oil extracted from the seed of Hura crepitans was characterized by an iodine value of 120.10 ± 0.70 g Iodine/100 g and a saponification number of 210.10 ± 0.40 mg KOH/g with the dominant fatty acid being C18:2 (52.8 ± 0.10%). The epoxidised fatty acid methyl esters prepared from the oil were used to synthesise the azidohydrin with a yield of 91.20%. The progress of the reaction was monitored and confirmed using FTIR and NMR. This showed the seed oil of Hura crepitans as a renewable resource that can be used to make valuable industrial and domestic products.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Azidohydrin from Hura crepitans Seed Oil: A Renewable Resource for Oleochemical Industry and Sustainable Development

Adewuyi

Göpfert

Wolff

et al. 2012

ISRN Organic Chemistry

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“…Analytical data of the product (rac-5bb) were identical with those reported in the literature. 24 Data for the Preparative Kinetic Resolution of rac-4b with 1c. After the filtration, the solvents were removed under reduced pressure.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Alcohol Cross-Coupling for the Kinetic Resolution of Diols via Oxidative Esterification

2015

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We present an organocatalytic C-O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, m-CPBA as the oxidant, and N,N'-diisopropylcarbodiimide as the activating agent. Racemic acyclic diols as well as trans-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols.

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“…Reactions in water and in micellar media are of interest and under attention from different views [28,29,34]. Along this line, we have used water as a medium for the reduction of carbonyl compounds and reductive amination of carbonyl compounds with [Zr(BH 4 ) 2 Cl 2 (dabco) 2 ] [11,12], ring opening reaction of epoxides [35a,b], addition of a water molecule to nitriles known as Ritter reactions [35c], Michael addition reactions [36] and oxidation of sulfides to sulfoxides [37].…”

Section: Reductive Amination Of Aldehydes and Ketones With [Zr(bh 4 )mentioning

confidence: 99%

Micellar media catalyzed highly efficient reductive amination of carbonyl compounds with bis(triphenylphosphine)(tetrahydroborato)zirconium(II), [Zr(BH4)2(Ph3P)2], as a new and a highly water tolerant tetrahydroborate reducing agent

Firouzabadi

Iranpoor

Alinezhad

2009

JICS

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RING OPENING OF EPOXIDES WITH CARBOXYLATES AND PHENOXIDES IN MICELLAR MEDIA CATALYZED WITH Ce(OTf)₄

Cited by 21 publications

References 38 publications

Synthesis of Azidohydrin from Hura crepitans Seed Oil: A Renewable Resource for Oleochemical Industry and Sustainable Development

Synthesis of Azidohydrin from Hura crepitans Seed Oil: A Renewable Resource for Oleochemical Industry and Sustainable Development

Alcohol Cross-Coupling for the Kinetic Resolution of Diols via Oxidative Esterification

Micellar media catalyzed highly efficient reductive amination of carbonyl compounds with bis(triphenylphosphine)(tetrahydroborato)zirconium(II), [Zr(BH4)2(Ph3P)2], as a new and a highly water tolerant tetrahydroborate reducing agent

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RING OPENING OF EPOXIDES WITH CARBOXYLATES AND PHENOXIDES IN MICELLAR MEDIA CATALYZED WITH Ce(OTf)4

Cited by 21 publications

References 38 publications

Synthesis of Azidohydrin from Hura crepitans Seed Oil: A Renewable Resource for Oleochemical Industry and Sustainable Development

Synthesis of Azidohydrin from Hura crepitans Seed Oil: A Renewable Resource for Oleochemical Industry and Sustainable Development

Alcohol Cross-Coupling for the Kinetic Resolution of Diols via Oxidative Esterification

Micellar media catalyzed highly efficient reductive amination of carbonyl compounds with bis(triphenylphosphine)(tetrahydroborato)zirconium(II), [Zr(BH4)2(Ph3P)2], as a new and a highly water tolerant tetrahydroborate reducing agent

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RING OPENING OF EPOXIDES WITH CARBOXYLATES AND PHENOXIDES IN MICELLAR MEDIA CATALYZED WITH Ce(OTf)₄