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1
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34248337349
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Visiting scientist from Dpto. Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain.
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Visiting scientist from Dpto. Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain.
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Pergamon Press: Oxford
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Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. Comprehensive Organic Synthesis, Vol.1; Pergamon Press: Oxford, 1991, 293-339.
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Olah, G.A.1
Krishnamurti, R.2
Prakash, G.K.S.3
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(a) Palomino, P. J. L.; Prakash, G. K. S.; Olah, G. A. Helv. Chim. Acta 2005, 88, 1221.
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Palomino, P.J.L.1
Prakash, G.K.S.2
Olah, G.A.3
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34248385102
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Even though triflic acid is expensive, the chemistry developed here is quite novel and useful
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(b) Even though triflic acid is expensive, the chemistry developed here is quite novel and useful.
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34248386349
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Arenes with electron-withdrawing substituents gave products in poor yields
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(c) Arenes with electron-withdrawing substituents gave products in poor yields.
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(a) Ishii, A.; Soloshonok, V. A.; Mikami, K. J. Org. Chem. 2000, 65, 1597.
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(b) Török, B.; Abid, M.; London, G.; Esquibel, J.; Török, M.; Mhadgut, S. C.; Yan, P.; Prakash, G. K. S. Angew. Chem. Int. Ed. 2005, 44, 3086.
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(2005)
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Abid, M.2
London, G.3
Esquibel, J.4
Török, M.5
Mhadgut, S.C.6
Yan, P.7
Prakash, G.K.S.8
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0025188085
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and related papers
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Takahashi, O.; Fukuhashi, K.; Fukumasa, M.; Hirai, T. Tetrahedron Lett. 1990, 31, 7031; and related papers.
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(1990)
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Takahashi, O.1
Fukuhashi, K.2
Fukumasa, M.3
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Feiring, A. E.; Crawford, M. K.; Farnham, W. B.; French, R. H.; Leffew, K. W.; Petrov, V. A.; Schadt, F. L. III; Tran, H. V.; Zumsteg, F. C. Macromolecules 2006, 39, 1443.
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(2006)
Macromolecules
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Feiring, A.E.1
Crawford, M.K.2
Farnham, W.B.3
French, R.H.4
Leffew, K.W.5
Petrov, V.A.6
Schadt III, F.L.7
Tran, H.V.8
Zumsteg, F.C.9
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Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Stratmann, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Daniels, R. E, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Jonson, B, Chen, W, Wong, M. W, Andres, J. L, Gonzalez, C, Head-Gordon, M, Pople, J. A. Gausian 98 Revision A.5, Gaussian, Inc, Pittsburg PA, 1998
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, R. E.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Jonson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Pople, J. A. Gausian 98 (Revision A.5); Gaussian, Inc.: Pittsburg PA, 1998.
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34248326726
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Becke's Three Parameter Hybid Method Using the LYP Correlation Functional: Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
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Becke's Three Parameter Hybid Method Using the LYP Correlation Functional: Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
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34248379974
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Typical Procedure for the Alkylation To a solution of benzene (1.2 mL, 13.5 mmol) and triflic acid (1.05 mL, 11.3 mmol) in 0.75 mL of CH 2Cl2, cooled to 0°C, a solution of 2-(trifluoromethyl)oxirane (2a, 0.126 g, 1.13 mmol) in CH 2Cl2 (0.75 mL) was added dropwise using a syringe over a period of 4 min with stirring. When the reaction mixture turned dark, the cooling bath was removed and the reaction mixture was allowed to come to r.t. The reaction mixture was then poured onto 10 g of crushed ice, made slightly basic with NaHCO3 and extracted with Et2O. The organic phase was washed with brine and H2O, and dried over anhyd MgSO 4. The residue obtained after concentration in vacuum was purified by flash column chromatography using a mixture of n-hexane and Et 2O (3:1) to obtain aαtrifluoromethyl-β-phenylethanol, 1,1,1-trifluoro-3-phenylpropan-2-ol3a
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1 =2.82 40 Hz
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