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Volumn , Issue 7, 2007, Pages 1158-1162

Friedel-Crafts alkylations of arenes with mono- and bis(trifluoromethyl) oxiranes in superacid medium: Facile synthesis of α-(trifluoromethyl)- and α,α-bis(trifluoromethyl)-β-arylethanols

Author keywords

Alkylation; Catalysis; Electrophilic aromatic substitutions; Epoxides; Ring opening

Indexed keywords

1,1,1 TRIFLUORO 3 (N PROPYLPHENYL)PROPAN 2 OL; 1,1,1 TRIFLUORO 3 PHENYLPROPAN 2 OL; 1,1,1 TRIFLUORO 3 TOLYLPROPAN 2 OL; 1,1,1,3,3,3 HEXAFLUORO 2 (METHYLBENZYL)PROPAN 2 OL; 1,1,1,3,3,3 HEXAFLUORO 2 (N PROPYLBENZYL)PROPAN 2 OL; 2 (2,5 DIEMTHYLBENZYL) 1,1,1,3,3,3 HEXAFLUOROPROPAN 2 OL; 2 (DIEMTHYLBENZYL) 1,1,1,3,3,3 HEXAFLUOROPROPAN 2 OL; 2 (ETHYLBENZYL) 1,1,1,3,3,3 HEXAFLUOROPROPAN 2 OL; 2 BENZYL 1,1,1,3,3,3 HEXAFLUOROPROPAN 2 OL; 3 (2,5 DIMETHYLPHENYL) 1,1,1 TRIFLUOROPROPAN 2 OL; 3 (DIMETHYLPHENYL) 1,1,1 TRIFLUOROPROPAN 2 OL; 3 ETHYLPHENYL 1,1,1 TRIFLUOROPROPAN 2 OL; ALCOHOL DERIVATIVE; ALPHA (TRIFLUOROMETHYL) BETA ARYLETHANOL DERIVATIVE; ALPHA,ALPHA BIS(TRIFLUOROMETHYL) BETA ARYLETHANOL DERIVATIVE; BIS(TRIFLUOROMETHYL)OXIRANE DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; MONO(TRIFLUOROMETHYL)OXIRANE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 34248346754     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977423     Document Type: Article
Times cited : (10)

References (34)
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    • Visiting scientist from Dpto. Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain.
    • Visiting scientist from Dpto. Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain.
  • 23
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    • Even though triflic acid is expensive, the chemistry developed here is quite novel and useful
    • (b) Even though triflic acid is expensive, the chemistry developed here is quite novel and useful.
  • 24
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    • Arenes with electron-withdrawing substituents gave products in poor yields
    • (c) Arenes with electron-withdrawing substituents gave products in poor yields.
  • 32
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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
    • 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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  • 34
    • 34248379974 scopus 로고    scopus 로고
    • 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
    • 1 =2.82 40 Hz


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