The Reaction of Aromatic—Aliphatic Sulfones with N-Bromosuccinimide<sup>1</sup>

Lotspeich, F. J.

doi:10.1021/jo01017a516

Cited by 11 publications

(4 citation statements)

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“…The oxidation of sulfide 3a to the sulfone 4a was studied using a range of typical sulfide-oxidizing reagents such as m -chloroperbenzoic acid ( m -CPBA), AcOH−H 2 O 2 , SeO 2 −H 2 O 2 , Oxone, and tetra- n -butylammonium Oxone under anhydrous conditions . For substrate 3a , the use of inexpensive Oxone (3 equiv) in a H 2 O/MeOH solvent mixture was most convenient.…”

Section: Resultsmentioning

confidence: 99%

“…For ease of workup and general applicability (see below), we decided to use the MnO 2 procedure for all subsequent studies. Optimized conditions involved microwave heating of a solution of 2-methylthiodihydropyrimidine 2a with 5 equiv of MnO 2 in anhydrous DCM under sealed-vessel conditions at 100 °C for 10 min 18 The oxidation of sulfide 3a to the sulfone 4a was studied using a range of typical sulfide-oxidizing reagents such as m-chloroperbenzoic acid (m-CPBA), 5 AcOH-H 2 O 2 , 19 SeO 2 -H 2 O 2 , 20 Oxone, 21 and tetra-n-butylammonium Oxone under anhydrous conditions. 22 For substrate 3a, the use of inexpensive Oxone (3 equiv) in a H 2 O/MeOH solvent mixture was most convenient.…”

Section: Resultsmentioning

confidence: 99%

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Microwave-Assisted Solution- and Solid-Phase Synthesis of 2-Amino-4-arylpyrimidine Derivatives

Matloobi¹,

Kappe²

2007

J. Comb. Chem.

103

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An efficient and rapid microwave-assisted solution-phase method for the synthesis of 2-amino-4-arylpyrimidine-5-carboxylic acid derivatives has been developed. The five-step linear protocol involves an initial Biginelli multicomponent reaction leading to dihydropyrimidine-2-thiones which are subsequently S-alkylated with methyl iodide. The resulting 2-methylthiodihydropyrimidines are sequentially oxidized first with manganese dioxide and then with Oxone to provide 2-methylsulfonyl-pyrimidines which serve as excellent precursors for the generation of a variety of 2-substituted pyrimidines via displacement of the reactive sulfonyl group with nitrogen, oxygen, sulfur, and carbon nucleophiles. A modified protocol using a solid-phase method has also been developed.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Microwave-Assisted Solution- and Solid-Phase Synthesis of 2-Amino-4-arylpyrimidine Derivatives

Matloobi¹,

Kappe²

2007

J. Comb. Chem.

103

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“…For the sake of comparison, 41 had to be previously made through the reduction of the 4-keto derivatives, since oxidation of the sulfur atom affected the alcohol group too. [47] We also ex-Scheme 11. Sulfones vs. sulfoxide formation.…”

Section: Reactions On Dialkyl Sulfidesmentioning

confidence: 99%

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Rozen

2005

Eur J Org Chem

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At present, HOF·CH3CN complex is the best oxygen transfer agent that chemistry has to offer. It is readily made by passing dilute fluorine through aqueous acetonitrile and does not require any isolation or purification. It is stable in aqueous acetonitrile solution for a few hours at room temperature, providing ample opportunities for various reactions. Epoxidation of regular olefins as well as of very electron‐depleted ones proceeds smoothly. HOF·CH3CN transfer oxygen also to heteroatoms, especially sulfur and nitrogen. Even very electron‐depleted sulfides such as RfSAr that are very difficult to oxidize, are converted into the respective sulfones in a matter of minutes. On the other hand, since the reaction conditions are very mild, the reagent can oxidize various thiophenes and amino acids to the corresponding S,S‐dioxides and α‐nitro acid derivatives. HOF·CH3CN was also instrumental in ending the 50 years quest for making the elusive 1,10‐phenanthroline N,N‐dioxide and for the novel transformation of azides to nitro derivatives. The use of BrF3 for making symmetric esters and of tBuOF as an electrophilic tert‐butoxylation agent is also mentioned. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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“…The sulfur atom reacts much faster then the hydroxyl moiety as well. Reacting thiochroman-4-ol ( 21 ) with 2.2 mol equiv of HOF·CH 3 CN produced, in higher than 90% yield, thiochroman-4-ol S,S -dioxide ( 22 ), which previously has had to be made through the reduction of the 4-keto derivative, since oxidation of the sulfur atom is difficult without affecting the hydroxyl group …”

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confidence: 99%

Oxidation of Sulfur-Containing Compounds with HOF·CH₃CN

Rozen

Bareket

1997

J. Org. Chem.

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The HOF·CH3CN complex, easily prepared by passing F2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. All types of sulfides have been oxidized to sulfones in excellent yields, in a few minutes at room temperature. The reaction proceeds through the formation of sulfoxides which at low temperatures of around −75 °C could be isolated in good yields. It was demonstrated through a reaction with thianthrene 5-oxide (20) that HOF·CH3CN is strongly electrophilic in nature. Sulfides with an electron-depleted sulfur atom such as perfluoroalkyl or aryl sulfides, which could not be well oxidized by any other method, were also efficiently converted to the corresponding sulfones in minutes. Thiophenes are generally hard to oxidize to the corresponding S-dioxides since the conditions required by the orthodox oxidants encourage consecutive typical ene and diene reactions. HOF·CH3CN requires short reaction times and low temperatures, thus enabling the isolation of thiophene dioxides, some of which could not be made by any other way. It seems that apart from unprotected amines, other functional groups such as aromatic rings, ketones, hydroxyls, and ethers do not interfere, since the sulfur atom reacts considerably faster.

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The Reaction of Aromatic—Aliphatic Sulfones with N-Bromosuccinimide¹

Cited by 11 publications

References 1 publication

Microwave-Assisted Solution- and Solid-Phase Synthesis of 2-Amino-4-arylpyrimidine Derivatives

Microwave-Assisted Solution- and Solid-Phase Synthesis of 2-Amino-4-arylpyrimidine Derivatives

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Oxidation of Sulfur-Containing Compounds with HOF·CH₃CN

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The Reaction of Aromatic—Aliphatic Sulfones with N-Bromosuccinimide1

Cited by 11 publications

References 1 publication

Microwave-Assisted Solution- and Solid-Phase Synthesis of 2-Amino-4-arylpyrimidine Derivatives

Microwave-Assisted Solution- and Solid-Phase Synthesis of 2-Amino-4-arylpyrimidine Derivatives

Elemental Fluorine and HOF·CH3CN in Service of General Organic Chemistry

Oxidation of Sulfur-Containing Compounds with HOF·CH3CN

Contact Info

Product

Resources

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The Reaction of Aromatic—Aliphatic Sulfones with N-Bromosuccinimide¹

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Oxidation of Sulfur-Containing Compounds with HOF·CH₃CN