메뉴 건너뛰기




Volumn , Issue 9, 1999, Pages 1403-1404

Facile substitution of N,N-dimethylanilines and phenols with trifluoroacetaldehyde ethyl hemiacetal

Author keywords

Aromatic substitution; N,N dimethylaniline; Phenol; Trifluoroacetaldehyde ethyl hemiacetal; trifluoromethylbenzylic alcohol

Indexed keywords

ACETALDEHYDE; ALCOHOL; CARBONIC ACID; IMIDAZOLE DERIVATIVE; N,N DIMETHYLANILINE; PHENOL DERIVATIVE; POTASSIUM;

EID: 0032872848     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2867     Document Type: Article
Times cited : (18)

References (29)
  • 2
    • 0027432004 scopus 로고
    • Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993. Resnati, G. Tetrahedron 1993, 49, 9385. Kitazume, T.; Lin, J. T.; Yamazaki, T. Tetrahedron: Asymmetry 1991, 2, 235. Banks, R. E. Ed. Preparation, Properties and Industrial Applications of Organofluorine Compounds, Ellis Horwood, Chichest, 1982.
    • (1993) Tetrahedron , vol.49 , pp. 9385
    • Resnati, G.1
  • 3
    • 0025822430 scopus 로고
    • Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993. Resnati, G. Tetrahedron 1993, 49, 9385. Kitazume, T.; Lin, J. T.; Yamazaki, T. Tetrahedron: Asymmetry 1991, 2, 235. Banks, R. E. Ed. Preparation, Properties and Industrial Applications of Organofluorine Compounds, Ellis Horwood, Chichest, 1982.
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 235
    • Kitazume, T.1    Lin, J.T.2    Yamazaki, T.3
  • 4
    • 0003616326 scopus 로고
    • Ellis Horwood, Chichest
    • Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993. Resnati, G. Tetrahedron 1993, 49, 9385. Kitazume, T.; Lin, J. T.; Yamazaki, T. Tetrahedron: Asymmetry 1991, 2, 235. Banks, R. E. Ed. Preparation, Properties and Industrial Applications of Organofluorine Compounds, Ellis Horwood, Chichest, 1982.
    • (1982) Preparation, Properties and Industrial Applications of Organofluorine Compounds
    • Banks, R.E.1
  • 5
    • 0032506573 scopus 로고    scopus 로고
    • Xu, Y.; Dolbier, Jr. W. R. Tetrahedron Lett. 1998, 39, 9151. Prakash, G. K.; Yudin, K. A. Chem. Rev. 1997, 97, 757. Loh, T. P.; Li, X. R. Tetrahedron Lett. 1997, 38, 869. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555. Konno, T.; Nakao, H.; Kitazume, T. J. Fluorine Chem. 1997, 86, 81. Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9151
    • Xu, Y.1    Dolbier W.R., Jr.2
  • 6
    • 0031140114 scopus 로고    scopus 로고
    • Xu, Y.; Dolbier, Jr. W. R. Tetrahedron Lett. 1998, 39, 9151. Prakash, G. K.; Yudin, K. A. Chem. Rev. 1997, 97, 757. Loh, T. P.; Li, X. R. Tetrahedron Lett. 1997, 38, 869. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555. Konno, T.; Nakao, H.; Kitazume, T. J. Fluorine Chem. 1997, 86, 81. Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579.
    • (1997) Chem. Rev. , vol.97 , pp. 757
    • Prakash, G.K.1    Yudin, K.A.2
  • 7
    • 0031016069 scopus 로고    scopus 로고
    • Xu, Y.; Dolbier, Jr. W. R. Tetrahedron Lett. 1998, 39, 9151. Prakash, G. K.; Yudin, K. A. Chem. Rev. 1997, 97, 757. Loh, T. P.; Li, X. R. Tetrahedron Lett. 1997, 38, 869. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555. Konno, T.; Nakao, H.; Kitazume, T. J. Fluorine Chem. 1997, 86, 81. Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 869
    • Loh, T.P.1    Li, X.R.2
  • 8
    • 0000532882 scopus 로고
    • Xu, Y.; Dolbier, Jr. W. R. Tetrahedron Lett. 1998, 39, 9151. Prakash, G. K.; Yudin, K. A. Chem. Rev. 1997, 97, 757. Loh, T. P.; Li, X. R. Tetrahedron Lett. 1997, 38, 869. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555. Konno, T.; Nakao, H.; Kitazume, T. J. Fluorine Chem. 1997, 86, 81. Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579.
    • (1990) Tetrahedron: Asymmetry , vol.1 , pp. 661
    • Bravo, P.1    Resnati, G.2
  • 9
    • 0026760246 scopus 로고
    • Xu, Y.; Dolbier, Jr. W. R. Tetrahedron Lett. 1998, 39, 9151. Prakash, G. K.; Yudin, K. A. Chem. Rev. 1997, 97, 757. Loh, T. P.; Li, X. R. Tetrahedron Lett. 1997, 38, 869. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555. Konno, T.; Nakao, H.; Kitazume, T. J. Fluorine Chem. 1997, 86, 81. Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579.
    • (1992) Tetrahedron , vol.48 , pp. 6555
    • McClinton, M.A.1    McClinton, D.A.2
  • 10
    • 0031256275 scopus 로고    scopus 로고
    • Xu, Y.; Dolbier, Jr. W. R. Tetrahedron Lett. 1998, 39, 9151. Prakash, G. K.; Yudin, K. A. Chem. Rev. 1997, 97, 757. Loh, T. P.; Li, X. R. Tetrahedron Lett. 1997, 38, 869. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555. Konno, T.; Nakao, H.; Kitazume, T. J. Fluorine Chem. 1997, 86, 81. Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579.
    • (1997) J. Fluorine Chem. , vol.86 , pp. 81
    • Konno, T.1    Nakao, H.2    Kitazume, T.3
  • 11
    • 0033515608 scopus 로고    scopus 로고
    • Xu, Y.; Dolbier, Jr. W. R. Tetrahedron Lett. 1998, 39, 9151. Prakash, G. K.; Yudin, K. A. Chem. Rev. 1997, 97, 757. Loh, T. P.; Li, X. R. Tetrahedron Lett. 1997, 38, 869. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555. Konno, T.; Nakao, H.; Kitazume, T. J. Fluorine Chem. 1997, 86, 81. Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579.
    • (1999) J. Org. Chem. , vol.64 , pp. 2579
    • Singh, R.P.1    Cao, G.2    Kirchmeier, R.L.3    Shreeve, J.M.4
  • 12
    • 0026156075 scopus 로고
    • Nohira, H. J. Synth. Org. Chem. Jpn. 1991, 49, 467. Walba, D. M.; Razavi, H. A.; Clark, N. A.; Parnar, D. S. J. Am. Chem. Soc. 1988, 110, 8686.
    • (1991) J. Synth. Org. Chem. Jpn. , vol.49 , pp. 467
    • Nohira, H.1
  • 15
    • 0001053318 scopus 로고
    • Creary, X. J. Org. Chem. 1987, 52, 5027. Fujisawa, T.; Ichikawa, K.; Shimizu, M. Tetrahedron: Asymmetry 1993, 4, 1237. Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267.
    • (1987) J. Org. Chem. , vol.52 , pp. 5027
    • Creary, X.1
  • 16
    • 0027195607 scopus 로고
    • Creary, X. J. Org. Chem. 1987, 52, 5027. Fujisawa, T.; Ichikawa, K.; Shimizu, M. Tetrahedron: Asymmetry 1993, 4, 1237. Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1237
    • Fujisawa, T.1    Ichikawa, K.2    Shimizu, M.3
  • 18
    • 0002600063 scopus 로고    scopus 로고
    • Loh, T. P.; Li, X. R. J. Chem. Soc., Chem. Commun. 1996, 1929. Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Sakumo, K.; Kuki, N.; Kuno, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Olah, G. A.; Wang, Q.; Li, X.-Y.; Parakash, G. K. S. Synlett 1993, 1, 32. Mikami, K.; Takasaki, T.; Matsukawa, S.; Maruta, M. Synlett 1995, 10, 1057.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 1929
    • Loh, T.P.1    Li, X.R.2
  • 19
    • 0026516861 scopus 로고
    • Loh, T. P.; Li, X. R. J. Chem. Soc., Chem. Commun. 1996, 1929. Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Sakumo, K.; Kuki, N.; Kuno, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Olah, G. A.; Wang, Q.; Li, X.-Y.; Parakash, G. K. S. Synlett 1993, 1, 32. Mikami, K.; Takasaki, T.; Matsukawa, S.; Maruta, M. Synlett 1995, 10, 1057.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1351
    • Kubota, T.1    Iijima, M.2    Tanaka, T.3
  • 20
    • 0001324783 scopus 로고    scopus 로고
    • Loh, T. P.; Li, X. R. J. Chem. Soc., Chem. Commun. 1996, 1929. Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Sakumo, K.; Kuki, N.; Kuno, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Olah, G. A.; Wang, Q.; Li, X.-Y.; Parakash, G. K. S. Synlett 1993, 1, 32. Mikami, K.; Takasaki, T.; Matsukawa, S.; Maruta, M. Synlett 1995, 10, 1057.
    • (1999) J. Fluorine Chem. , vol.93 , pp. 165
    • Sakumo, K.1    Kuki, N.2    Kuno, T.3    Takagi, T.4    Koyama, M.5    Ando, A.6    Kumadaki, I.7
  • 21
    • 85064426949 scopus 로고
    • Loh, T. P.; Li, X. R. J. Chem. Soc., Chem. Commun. 1996, 1929. Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Sakumo, K.; Kuki, N.; Kuno, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Olah, G. A.; Wang, Q.; Li, X.-Y.; Parakash, G. K. S. Synlett 1993, 1, 32. Mikami, K.; Takasaki, T.; Matsukawa, S.; Maruta, M. Synlett 1995, 10, 1057.
    • (1993) Synlett , vol.1 , pp. 32
    • Olah, G.A.1    Wang, Q.2    Li, X.-Y.3    Parakash, G.K.S.4
  • 22
    • 2742513913 scopus 로고
    • Loh, T. P.; Li, X. R. J. Chem. Soc., Chem. Commun. 1996, 1929. Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Sakumo, K.; Kuki, N.; Kuno, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Olah, G. A.; Wang, Q.; Li, X.-Y.; Parakash, G. K. S. Synlett 1993, 1, 32. Mikami, K.; Takasaki, T.; Matsukawa, S.; Maruta, M. Synlett 1995, 10, 1057.
    • (1995) Synlett , vol.10 , pp. 1057
    • Mikami, K.1    Takasaki, T.2    Matsukawa, S.3    Maruta, M.4
  • 23
    • 0000187933 scopus 로고
    • Fujii, S.; Maki, Y.; Kimoto, H. J. Fluorine Chem. 1986, 30, 415. Maki, Y.; Kimoto, H.; Fujii, S.; Senga, M.; Cohen, L. A. J. Fluorine Chem. 1988, 39, 47.
    • (1986) J. Fluorine Chem. , vol.30 , pp. 415
    • Fujii, S.1    Maki, Y.2    Kimoto, H.3
  • 25
    • 0344226427 scopus 로고    scopus 로고
    • note
    • 2 to give the pure compound 3a.
  • 26
    • 0345520147 scopus 로고    scopus 로고
    • note
    • 3 C% 54.77; H% 5.52, N% 6.39. Found C% 54.56, H% 5.46, N% 6.55.
  • 27
    • 0345520148 scopus 로고    scopus 로고
    • note
    • 4. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (9:1 to 5:1 hexane: EtOAc), 6a (0.58g, 10%) and 4a (3.74g, 65%) being collected.
  • 28
    • 0345520146 scopus 로고    scopus 로고
    • note
    • +, 55), 174 (18), 146 (40), 123 (95), 77 (100). HRMS. Calculated: 192.0398. Found: 192.0378.
  • 29
    • 0344657822 scopus 로고    scopus 로고
    • note
    • +, 60), 151 (100). HRMS. Calculated: 220.0711. Found: 220.0711.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.