Poly(vinylpyridinium dichromate): an inexpensive recyclable polymeric reagent

Fréchet, Jean M. J.; Darling, Pauline; Farrall, M. Jean

doi:10.1021/jo00321a042

Cited by 123 publications

(41 citation statements)

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“…Since N-benzylidenebenzenesulfin-A C H T U N G T R E N N U N G amide is known to be more stable than N-benzyl-A C H T U N G T R E N N U N G idenebenzenesulfonamide and could be instantaneously converted to the latter by reaction with m-CPBA, [17] we decided to synthesize polymer 5 (Scheme 1, route B). Different reaction conditions were examined (Table 2, entries 5-8) and we were pleased to find that using TiA C H T U N G T R E N N U N G (OEt) 4 under microwave irradiation gave 100% conversion within 2 min. Polymer 5 was subsequently oxidized directly to polymer 1 using m-CPBA/KOH.…”

Section: Resultsmentioning

confidence: 99%

“…The configuration of 16c was determined by comparing the 1 H NMR spectrum of 16c with the 1 H NMR spectrum of the compound reported earlier. [23] For the enamine oxidation, 1-(1,2-diphenylvinyl)-pyrrolidine 15e, prepared by standard methods using TiCl 4 , [24] was treated with polymer 1 (1.1 equiv.) in CHCl 3 at ambient temperature for 6 h to give 1,2-diphenyl-2-pyrrolidinylethanone 16e (Table 10, entry 4).…”

Section: Oxidation Of Enolates and Enaminesmentioning

confidence: 99%

“…[1d,2] Amongst them, a number of oxidants, such as IBX, [3] trimethylamine oxide, [4] dichromate, [5] and Swern oxidants [6] have been developed. However, to the best of our knowledge, the potential of polymer-supported Nphenylsulfonyloxaziridine has not been explored.…”

Section: Introductionmentioning

confidence: 99%

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Polymer‐Supported N‐Phenylsulfonyloxaziridine (Davis Reagent): A Versatile Oxidant

Gao¹,

Lam²

2008

Adv Synth Catal

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An efficient preparation of a new recyclable polymer-supported oxidizing agent based on Nphenylsulfonyloxaziridine has been developed. This new polymer-supported oxidant was shown to effect a clean and selective conversion of a range of sulfides, selenides, amines, phosphines and enolates to the corresponding sulfoxides, selenoxides, N-oxides, phosphine oxides and a-hydroxy carbonyl compounds. It also enabled tetrahydrobenzimidazoles to be oxidatively rearranged to spiro-fused 5-imidazolones. Recycling of the polymer-supported oxidant is possible with minimal loss of activity after several reoxidations.

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Section: Resultsmentioning

confidence: 99%

Section: Oxidation Of Enolates and Enaminesmentioning

confidence: 99%

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Polymer‐Supported N‐Phenylsulfonyloxaziridine (Davis Reagent): A Versatile Oxidant

Gao¹,

Lam²

2008

Adv Synth Catal

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“…6,[10][11][12] These copolymers have the advantage of complexing different oxidizing agents by immobilizing them. [13][14][15] The 2VP or 4VP-DVB copolymer beads are synthesized by suspension polymerization technique and the porosity in the beads is controlled by mixing some inert organic liquid named diluent with monomers. [12][13][14][15][16][17][18] Two of the most desirable properties of any ion-exchanger are: high ionexchange capacity and fast ion-exchange kinetics.…”

Section: Introductionmentioning

confidence: 99%

“…[13][14][15] The 2VP or 4VP-DVB copolymer beads are synthesized by suspension polymerization technique and the porosity in the beads is controlled by mixing some inert organic liquid named diluent with monomers. [12][13][14][15][16][17][18] Two of the most desirable properties of any ion-exchanger are: high ionexchange capacity and fast ion-exchange kinetics. These characteristics could be obtained in the network materials by the functional groups present in the chemical structure and by their porosity.…”

Section: Introductionmentioning

confidence: 99%

Quaternization reaction of 2-vinylpyridine and 4-vinylpyridine network copolymers for 4-nitrophenol adsorption

Rodrigues

Aguiar

2007

J. Braz. Chem. Soc.

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Este artigo avalia o emprego de copolímeros porosos (a base de estireno-STY e vinilpiridina-VP, reticulados com divinilbenzeno-DVB) como adsorventes de 4-nitrofenol de soluções aquosas. Os copolímeros foram sintetizados através de polimerização em suspensão aquosa via radical livre na presença de heptano (HEP) e tolueno (TOL) em diferentes proporções como agentes porogênicos. As unidades de VP nos copolímeros foram modificadas quimicamente pela adição eletrofílica de monômeros vinílicos funcionalizados (acrilonitrila). Os copolímeros quaternizados foram caracterizados por espectrofotometria na região do infravermelho (FTIR), análise elementar (CHN), microscopia ótica (OM) e microscopia eletrônica de varredura (SEM).This article aims to evaluate porous copolymers (based on styrene-STY and vinylpyridine-VP, cross-linked with divinylbenzene-DVB) as adsorbents for 4-nitrophenol from aqueous solution. These copolymers were synthesized by suspension polymerizations in the presence of heptane (HEP) and toluene (TOL) in different proportions as porogenic agents. The VP units of the copolymers were chemically modified by the addition of the electrophilic ethylenic compound (acrylonitrile). The quaternized copolymers were characterized by infrared spectrometry (FTIR), elemental analysis (CHN), optical microscopy (OM) and scanning electron microscopy (SEM).

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Solid-supported reagents in organic synthesis

Drewry¹,

Coe²,

Poon³

1999

Med. Res. Rev.

139

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The current interest in solid-phase organic synthesis has led to a renewed interest in a complementary technique in which solid supported reagents are used in solution phase chemistry. This technique obviates the need for attachment of the substrate to a solid-support, and enables the chemist to monitor the reactions using familiar analytical techniques. The purpose of this review is to increase awareness of the wide range of useful transformations which can be accomplished using solid-supported reagents.

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Poly(vinylpyridinium dichromate): an inexpensive recyclable polymeric reagent

Cited by 123 publications

References 0 publications

Polymer‐Supported N‐Phenylsulfonyloxaziridine (Davis Reagent): A Versatile Oxidant

Polymer‐Supported N‐Phenylsulfonyloxaziridine (Davis Reagent): A Versatile Oxidant

Quaternization reaction of 2-vinylpyridine and 4-vinylpyridine network copolymers for 4-nitrophenol adsorption

Solid-supported reagents in organic synthesis

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