2,4,6‐Triphenylpyrylium Tetrafluoroborate
作者： Alexandru T. Balaban
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摘要: [448-61-3] C23H17BF4O (MW 396.21) InChI = 1S/C23H17O.BF4/c1-4-10-18(11-5-1)21-16-22(19-12-6-2-7-13-19)24-23(17-21)20-14-8-3-9-15-20;2-1(3,4)5/h1-17H;/q+1;-1 InChIKey = VQYPWMWEJGDSTF-UHFFFAOYSA-N (converts primary amines into pyridinium salts which on reaction with nucleophiles NuH afford RNu) Physical Data: mp 255–257 °C. Solubility: insol H2O, EtOH, Et2O; sol CF3CO2H. Form Supplied in: yellow solid. Purification: recryst. from AcOH or (ClCH2)2. Handling, Storage, and Precautions: may be stored indefinitely. Reports possible mutagenic activity make it desirable to avoid direct contact skin. Other 2,4,6-triphenylpyrylium are the commercially available sulfoacetate, hydrogen sulfate whose synthesis2 is analogous that of 1 as described by eq below.
sci-hub.se 参考文章(52)
A.T. Balaban, W. Schroth, G. Fischer, Pyrylium Salts Part I. Syntheses Advances in Heterocyclic Chemistry. ,vol. 10, pp. 241- 326 ,(1969) , 10.1016/S0065-2725(08)60499-7
A.T. Balaban, Reaction of pyrylium salts with nucleophiles—VII Tetrahedron. ,vol. 24, pp. 5059- 5065 ,(1968) , 10.1016/S0040-4020(01)88416-7
A.T. Balaban, Reaction of pyrylium salts with nucleophiles—IX : Formation of 1,2-diazepine or 2-pyrazoline derivatives from 2,4,6-triphenylpyrylium salts and hydrazine Tetrahedron. ,vol. 26, pp. 739- 742 ,(1970) , 10.1016/S0040-4020(01)97869-X
Alan R. Katritzky, Pedro Molina-Buendia, Heterocycles in organic synthesis. Part 23. 1-Amino-4,6-diphenyl-2-pyridone: a new reagent for the conversion of aldehydes into nitriles Journal of The Chemical Society-perkin Transactions 1. ,vol. 10, pp. 1957- 1960 ,(1979) , 10.1039/P19790001957
Alan R. Katritzky, Karoly Horvath, Bernard Plau, Reductive deamination of primary amines Journal of the Chemical Society, Perkin Transactions 1. ,vol. 12, pp. 2554- 2560 ,(1980) , 10.1039/P19800002554
Alan R. Katritzky, George Z. de Ville, Ranjan C. Patel, The SRN2 mechanism of nucleophilic substitution Tetrahedron Letters. ,vol. 21, pp. 1723- 1726 ,(1980) , 10.1016/S0040-4039(00)77820-8
Alan R. Katritzky, Sukhpal S. Thind, The synthesis and reactions of sterically constrained pyrylium and pyridinium salts Journal of the Chemical Society, Perkin Transactions 1. ,vol. 11, pp. 1895- 1900 ,(1980) , 10.1039/P19800001895
Alan R. Katritzky, Giuseppe Musumarra, New insights into aliphatic nucleophilic substitution reactions from the use of pyridines as leaving groups Chemical Society Reviews. ,vol. 13, pp. 47- 68 ,(1984) , 10.1039/CS9841300047
Alan R. Katritzky, Conversions of primary amino groups into other functionality mediated by pyrylium cations Tetrahedron. ,vol. 36, pp. 679- 699 ,(1980) , 10.1016/S0040-4020(01)93679-8
Alan R. Katritzky, Gaietano Liso, Edward Lunt, Ranjan C. Patel, Sukhpal S. Thind, Abid Zia, Heterocycles in organic synthesis. Part 42. Preparation of azides, phthalimides, and sulphonamides from primary amines Journal of The Chemical Society-perkin Transactions 1. ,vol. 11, pp. 849- 851 ,(1980) , 10.1039/P19800000849