55434-48-5

Usage

Uses

Used in Organic Chemistry:
2,4,6-Triphenyl-2H-thiopyran is used as a building block for the synthesis of more complex organic molecules, leveraging its unique structure to create new compounds with potential applications in various fields.
Used in Material Science:
In the field of material science, 2,4,6-Triphenyl-2H-thiopyran is utilized as a component in the development of new materials, taking advantage of its structural properties to enhance material characteristics and performance.
Used in Research and Development:
2,4,6-Triphenyl-2H-thiopyran serves as an interesting target for further research, with its unique structure and properties offering opportunities for exploration in various scientific and industrial applications. This includes potential uses in pharmaceuticals, chemical engineering, and other specialized areas where novel compounds are sought after for their specific properties.

Upstream product

• 7584-36-3 2,4,6-triphenyl-4H-thiopyran 
• 2930-37-2 2,4,6-triphenylthiopyrylium perchlorate 

Relevant academic research and scientific papers

Efficient reduction of thiopyrylium salts to corresponding 2H- and 4H-thiopyrans under solvent-free condition: Regioselectivity and mechanism

A solvent-free reduction of 2,4,6-triarylthiopyrylium with NaBH 4/alumina is described. The regioselectivity of these reductions were compared with those obtained in solution experiments. Copyright Taylor & Francis Inc.

Improved intermolecular hydride transfer using task-specific ionic liquid: A reasonable and environmentally benign approach for the synthesis of bioactive 2H-thiopyran derivatives

The present study describes, for the first time, the application of 1-n-butyl-3-methylimidazolium borohydride ([bmim]BH4) as task-specific ionic liquid for highly regioselective reduction of triarylthiopyrylium salts. This method furnished a straightforwa

Substituent effects in reductions of heteroaromatic cations

A set of 11 each of 2,4,6-triphenylpyrylium, -thiopyrylium and -N-methylpyridinium tetrafluoroborates carrying a range of substituents in the phenyl rings were prepared. First and second wave reduction potentials were determined. For the thiopyrylium seri

Substituent effects in cyanoborohydride reductions of heterocyclic aromatic cations

First and second wave E1/2redn potentials have been measured by cyclic voltammetry for a set of fifteen 2,6-diphenyl-4-(X-phenyl)-pyrylium, -thiopyrylium and -N-methylpyridinium tetrafluoroborates, with X = p-CH3, -H, m-Cl, p-CF3 and m,m-(CF3)2.There are linear correlations between Hammett substituent constants and scaled potentials (E/0.05915) giving slopes of ρ = 2.59+/-0.06 (r2 = 0.9984), 2.38+/-0.07 (r2 = 0.9973) and 3.10+/-0.16 (r2 = 0.9918), respectively, for the first wave potentials.Products, rates and kinetic hydrogen isotope effects for reductions of the cations with sodium and tetrabutylammonium cyanoborohydride in acetonitrile solution have been determined.Reaction of the thiopyrylium 2 (X = H) yields kinetically controlled 54:46 mixture of the 4H- and 2H-thiopyrans.With the pyrylium ion 1 (X = H) the 4H- to 2H-ratio is 24:76 with the 2H-pyran suffering electrocyclic ring opening to 1,3,5-triphenylpentadienal.Product ratios are weakly sensitive to substituents on the 4-phenyl, with electron withdrawing groups increasing the amount of 2H-product for both thiopyryliums and pyrylium cations.Reductions are first order in cation and cyanoborohydride.For sodium cyanoborohydride and 2,4,6-triphenylpyrylium, k(25 deg C) = 65.6 dm3 mol-1 s-1 and for 2,4,6-triphenylthiopyrylium. k(25 deg C) = 16.7 dm3 mol-1 s-1, with kinetic isotope effects kBH3CN/kBD3CN) of 1.17 and 1.68, respectively.Logarithms of rate constants correlate with Hammett constants giving ρ = 1.46+/-0.06 (r2 = 0.9951) for the pyrylium series and ρ = 1.12+/-0.08 (r2 = 0.9831) for the thiopyryliums.The N-methylpyridinium ions do not react with cyanoborohydride.The X-ray crystal structure of 2,4,6-triphenyl-N-methylpyridinium tetrafluoroborate has been determined.Dihedral angles about bonds from the pyridinium ring to the 2- and 6-phenyls are larger than corresponding angles in 2,4,6-triphenylpyrylium and 2,4,6-triphenylthiopyryliums and are ascribed to relief of non-bonded interactions between the 2- and 6-phenyls and the N-methyl group.

Kinetics and Mechanism of the Isomerisation of 2,4,6-Triphenyl-4H-Thiopyran

Isomerization of 2,4,6-triphenyl-4H-thiopyran into 2,4,6-triphenyl-2H-thiopyran has been studied kinetically and the rate of the reaction was determined in dimethylformamide.The first order rate constant could be expressed in terms of the Arrhenius parameters by the equation k1 = 2.85 x 107 e-15820+/-110/RT.