Polymer supported reagents. Chromic acid on anion exchange resins. A simple and practical oxidation of alcohols to aldehydes and ketones

Cainelli, Gianfranco; Cardillo, Giuliana; Orena, Mario; Sandri, Sergio

doi:10.1021/ja00437a071

Cited by 155 publications

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“…12,13 Many useful procedures for the oxidation of alcohols to the corresponding carbonyl compounds using polymer supported reagents have been reported. 14,15 Our interest in polymer-supported reactions 16 and synthesis of polymeric analogues of well known halogeno-sulfonamides and their applications have been reported. 17 A macro porous poly(styrene-co-divinylbenzene) resin having N,N-dichloro sulfonamide groups [18][19][20] have been used as a polymer supported reagent for chlorination, oxidation for residual sulfides, 21 cyanides, 22 thiocyanates, 23 water disinfection, 18 and some application in synthetic organic chemistry.…”

mentioning

confidence: 99%

Polymeric decontaminant 2 (N,N‐dichloropolystyrene sulfonamide): Synthesis, characterization, and efficacy against simulant of sulfur mustard

Gutch

Srivastava

Sekhar

2007

J of Applied Polymer Sci

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A polymeric decontaminant N,N-dichloropolystyrene sulfonamide was synthesized by different steps from starting material polystyrene and followed by sulfonation, chlorosulfonation, and amidification. Halogeno-sulfonamide was obtained by treatment of sodium hypochlorite with sulfonamide resin. It was characterized by FTIR, solubility, viscosity, DSC, and TGA techniques. Efficiency of this polymer as decontaminant was evaluated by reaction with 2-chloro ethyl phenyl sulfide, a simulant of sulfur mustard (SM) at room temperature. This decontamination reaction was monitored by gas chromatography (GC) and products were identified by gas chromatography-mass spectrometry (GC-MS). The positive chlorine content of this polymer was checked by standard iodometry titration. The synthesized positive chlorine compound is observed to be a promising decontaminant against simulant of sulfur mustard, chiefly in the situation where use of aqueous medium such as acetonitrile : water (2 : 1) is precluded.

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confidence: 99%

Polymeric decontaminant 2 (N,N‐dichloropolystyrene sulfonamide): Synthesis, characterization, and efficacy against simulant of sulfur mustard

Gutch

Srivastava

Sekhar

2007

J of Applied Polymer Sci

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“…But if the oxidant is supported on a polymer, which has certain advantages [9] over homogeneous reactions, the mechanism would be preferably according to Scheme (1).…”

Section: Discussionmentioning

confidence: 99%

“…The polymeric reagent (oxidant) was synthesized according to the reported procedure [9][10][11] starting from the chloride form of Amberlyst A-26 [a microreticular anion exchange resin (Fluka 20-50 mesh)].…”

Section: Preparation Of Polymer Bound -Chromium(vi) Oxidementioning

confidence: 99%

Kinetics and mechanism of oxidation of substituted benzyl alcohols by polymer supported chromic acid

Hilage

2005

Transition Met Chem

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The reactions between substituted benzyl alcohols were found to proceed through ester formation. The ester thus formed decomposes in a slow step to produce chromium(IV). Since our oxidant was supported on a polymeric material the intermediate chromium(IV) will further oxidize another molecule of alcohol generating a free radical in a fast step. The free radical subsequently reacts with another oxidant site in the polymeric reagent in a fast step leading to the formation of chromium(V). The intermediate chromium(V) in the last step reacts with alcohol to produce an aldehyde. The activation parameters were also determined and the mechanism is predicted.

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“…Unfortunately N,N-dialkylated aminoalcohols seem to be inapplicable for this method due to complete decomposition of the starting material within 15 minutes. [30] Finally, this reagent system allows one to oxidize secondary aryl-substituted as well as aliphatic alcohols 7,21] are strong oxidants with comparable reactivity to our reagent system, the polystyrene-based versions tend to decompose which results in substantial contamination of the solution and difficulties during the filtration. On the other hand, immobilization of the permanganate(VII) anion to exchange resins [8,21] leads to an oxidant which allows one to transform allylic and benzylic alcohols to the corresponding aldehydes but fails to effectively oxidize secondary alcohols.…”

Section: Full Papersmentioning

confidence: 99%

Polymer‐Supported Bisacetoxybromate(I) Anion –‐An Efficient Co‐Oxidant in the TEMPO‐Mediated Oxidation of Primary and Secondary Alcohols

2003

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A polymer-bound reagent for the efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones in the presence of a catalytic amount of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) is described. The oxidation process is particular mild and allows one to prepare aldehydes with a-chirality without racemization. This also includes the synthesis of a-aminoaldehydes. In most cases, work-up of this heavy metal-free oxidation is achieved by simple filtration followed by removal of the solvent. Insight into the role of the bromate(I) anion in the oxidation process was gained from the TEMPO-mediated oxidation of benzaldehyde in the presence of the hypochlorite anion loaded on an anion exchange resin.

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Polymer supported reagents. Chromic acid on anion exchange resins. A simple and practical oxidation of alcohols to aldehydes and ketones

Cited by 155 publications

References 0 publications

Polymeric decontaminant 2 (N,N‐dichloropolystyrene sulfonamide): Synthesis, characterization, and efficacy against simulant of sulfur mustard

Polymeric decontaminant 2 (N,N‐dichloropolystyrene sulfonamide): Synthesis, characterization, and efficacy against simulant of sulfur mustard

Kinetics and mechanism of oxidation of substituted benzyl alcohols by polymer supported chromic acid

Polymer‐Supported Bisacetoxybromate(I) Anion –‐An Efficient Co‐Oxidant in the TEMPO‐Mediated Oxidation of Primary and Secondary Alcohols

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