Organic reactions without an organic medium: Utilization of perfluorotriethylamine as a reaction medium

Green Chemistry

Volumn 1, Issue 1, 1999, Pages 21-22

  Nakano, Hirofumi ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033416886     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808193j     Document Type: Article

References (23)

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7. D.-W. Zhu, Synthesis, 1993, 953; I. T. Horváth and J. Rábai, Science, 1994, 266, 72; S. Halida and D. P. Curran, J. Am. Chem. Soc., 1996, 118, 2531; S. G. DiMagno, P. H. Dussault and J. A. Schultz, J. Am. Chem. Soc., 1996, 118, 5312; A. Studer, S. Halida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D. P. Curran, Science, 1997, 275, 823; A. Studer, P. Jeger, P. Wipf and D. P. Curran, J. Org. Chem., 1997, 62, 2917; I. Klement, H. Lütjens and P. Knochel, Angew. Chem., Int. Ed. Engl, 1997, 36, 1454; J. J. J. Juliette, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1610; M.-A. Guillevic, A. M. Arif, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1612; J.-M. Vincent, A. Rabion, V. K. Yachandra and R. H. Fish, ibid., 1997, 36, 2346; B. Betzemeier and P. Knochel, ibid., 1997, 36, 2623; M. Hoshino, P. Degenkolb and D. P. Curran, J. Org. Chem., 1997, 62, 8341.
8. D.-W. Zhu, Synthesis, 1993, 953; I. T. Horváth and J. Rábai, Science, 1994, 266, 72; S. Halida and D. P. Curran, J. Am. Chem. Soc., 1996, 118, 2531; S. G. DiMagno, P. H. Dussault and J. A. Schultz, J. Am. Chem. Soc., 1996, 118, 5312; A. Studer, S. Halida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D. P. Curran, Science, 1997, 275, 823; A. Studer, P. Jeger, P. Wipf and D. P. Curran, J. Org. Chem., 1997, 62, 2917; I. Klement, H. Lütjens and P. Knochel, Angew. Chem., Int. Ed. Engl, 1997, 36, 1454; J. J. J. Juliette, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1610; M.-A. Guillevic, A. M. Arif, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1612; J.-M. Vincent, A. Rabion, V. K. Yachandra and R. H. Fish, ibid., 1997, 36, 2346; B. Betzemeier and P. Knochel, ibid., 1997, 36, 2623; M. Hoshino, P. Degenkolb and D. P. Curran, J. Org. Chem., 1997, 62, 8341.
9. D.-W. Zhu, Synthesis, 1993, 953; I. T. Horváth and J. Rábai, Science, 1994, 266, 72; S. Halida and D. P. Curran, J. Am. Chem. Soc., 1996, 118, 2531; S. G. DiMagno, P. H. Dussault and J. A. Schultz, J. Am. Chem. Soc., 1996, 118, 5312; A. Studer, S. Halida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D. P. Curran, Science, 1997, 275, 823; A. Studer, P. Jeger, P. Wipf and D. P. Curran, J. Org. Chem., 1997, 62, 2917; I. Klement, H. Lütjens and P. Knochel, Angew. Chem., Int. Ed. Engl, 1997, 36, 1454; J. J. J. Juliette, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1610; M.-A. Guillevic, A. M. Arif, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1612; J.-M. Vincent, A. Rabion, V. K. Yachandra and R. H. Fish, ibid., 1997, 36, 2346; B. Betzemeier and P. Knochel, ibid., 1997, 36, 2623; M. Hoshino, P. Degenkolb and D. P. Curran, J. Org. Chem., 1997, 62, 8341.
10. D.-W. Zhu, Synthesis, 1993, 953; I. T. Horváth and J. Rábai, Science, 1994, 266, 72; S. Halida and D. P. Curran, J. Am. Chem. Soc., 1996, 118, 2531; S. G. DiMagno, P. H. Dussault and J. A. Schultz, J. Am. Chem. Soc., 1996, 118, 5312; A. Studer, S. Halida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D. P. Curran, Science, 1997, 275, 823; A. Studer, P. Jeger, P. Wipf and D. P. Curran, J. Org. Chem., 1997, 62, 2917; I. Klement, H. Lütjens and P. Knochel, Angew. Chem., Int. Ed. Engl, 1997, 36, 1454; J. J. J. Juliette, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1610; M.-A. Guillevic, A. M. Arif, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1612; J.-M. Vincent, A. Rabion, V. K. Yachandra and R. H. Fish, ibid., 1997, 36, 2346; B. Betzemeier and P. Knochel, ibid., 1997, 36, 2623; M. Hoshino, P. Degenkolb and D. P. Curran, J. Org. Chem., 1997, 62, 8341.
11. D.-W. Zhu, Synthesis, 1993, 953; I. T. Horváth and J. Rábai, Science, 1994, 266, 72; S. Halida and D. P. Curran, J. Am. Chem. Soc., 1996, 118, 2531; S. G. DiMagno, P. H. Dussault and J. A. Schultz, J. Am. Chem. Soc., 1996, 118, 5312; A. Studer, S. Halida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D. P. Curran, Science, 1997, 275, 823; A. Studer, P. Jeger, P. Wipf and D. P. Curran, J. Org. Chem., 1997, 62, 2917; I. Klement, H. Lütjens and P. Knochel, Angew. Chem., Int. Ed. Engl, 1997, 36, 1454; J. J. J. Juliette, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1610; M.-A. Guillevic, A. M. Arif, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1612; J.-M. Vincent, A. Rabion, V. K. Yachandra and R. H. Fish, ibid., 1997, 36, 2346; B. Betzemeier and P. Knochel, ibid., 1997, 36, 2623; M. Hoshino, P. Degenkolb and D. P. Curran, J. Org. Chem., 1997, 62, 8341.
12. D.-W. Zhu, Synthesis, 1993, 953; I. T. Horváth and J. Rábai, Science, 1994, 266, 72; S. Halida and D. P. Curran, J. Am. Chem. Soc., 1996, 118, 2531; S. G. DiMagno, P. H. Dussault and J. A. Schultz, J. Am. Chem. Soc., 1996, 118, 5312; A. Studer, S. Halida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D. P. Curran, Science, 1997, 275, 823; A. Studer, P. Jeger, P. Wipf and D. P. Curran, J. Org. Chem., 1997, 62, 2917; I. Klement, H. Lütjens and P. Knochel, Angew. Chem., Int. Ed. Engl, 1997, 36, 1454; J. J. J. Juliette, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1610; M.-A. Guillevic, A. M. Arif, I. T. Horváth and J. A. Gladysz, ibid., 1997, 36, 1612; J.-M. Vincent, A. Rabion, V. K. Yachandra and R. H. Fish, ibid., 1997, 36, 2346; B. Betzemeier and P. Knochel, ibid., 1997, 36, 2623; M. Hoshino, P. Degenkolb and D. P. Curran, J. Org. Chem., 1997, 62, 8341.
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17. For reviews, see: A. Hosomi, Acc. Chem. Res., 1988, 21, 200; I. Fleming, J. Dunogues and R. Smithers, Org. React., 1989, 37, 57.
18. 99%; 85% n-isomer; bp = 57°C.
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23. 4 and concentrated in vacua. Purification of the residue by silica gel chromatography afforded the homoallyl alcohol.