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Volumn 52, Issue 19, 1987, Pages 4230-4234

An Assessment of The Causes of The “Cesium Effect”

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EID: 33845282801     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00228a015     Document Type: Article
Times cited : (235)

References (27)
  • 1
    • 85022681293 scopus 로고
    • Properties of cesium carbonate
    • Gmelin's Handbuch der Anorganischen Chemie, 8th ed.; Verlag Chemie: Weinheim, FRG
    • Properties of cesium carbonate: Gmelin's Handbuch der Anorganischen Chemie, 8th ed.; Verlag Chemie: Weinheim, FRG, 1936; Vol. 25, pp 234–236.
    • (1936) , vol.25 , pp. 234-236
  • 4
    • 33845556522 scopus 로고
    • Buter, J.; Kellogg, R. M. Org. Synth., in press. Lemaire, M.; Vriesema, B. K.; Kellogg, R. M. Tetrahedron Lett. 1985, 6, 3499. Vriesema, B. K.; Lemaire, M.; Buter, J.; Kellogg, R. M. J. Org. Chem. 1986, 51, 5169.
    • Buter, J.; Kellogg, R. M. J. Org. Chem. 1981, 46, 4481. Buter, J.; Kellogg, R. M. Org. Synth., in press. Lemaire, M.; Vriesema, B. K.; Kellogg, R. M. Tetrahedron Lett. 1985, 6, 3499. Vriesema, B. K.; Lemaire, M.; Buter, J.; Kellogg, R. M. J. Org. Chem. 1986, 51, 5169.
    • (1981) J. Org. Chem. , vol.46 , pp. 4481
    • Buter, J.1    Kellogg, R.M.2
  • 6
    • 85022733360 scopus 로고    scopus 로고
    • In ethanolic solution, ethyl acetoacetate, diethyl malonate
    • and tosylmethyl isocyanide are slowly deprotonated by cesium carbonate: unpublished results.
    • In ethanolic solution, ethyl acetoacetate, diethyl malonate, and tosylmethyl isocyanide are slowly deprotonated by cesium carbonate: Van Keulen, B. J., unpublished results.
    • Keulen, B.J.1
  • 10
    • 0000588080 scopus 로고
    • Lerchen, H. G.; Kunz, H. Tetrahedron Lett. 1985, 26, 5257. Huffman, J.; Desai, R. Synth. Commun. 1983, 13, 553. Torisawa, Y.; Okabe, H.; Ikegami, S. Chem. Lett. 1984, 1555. For a somewhat different application, see: Keinan, E.; Eren, D. J. Org. Chem. 1986, 51, 3165. Cainelli, G.; Manescalchi, F.; Martelli, G.; Panunzio, M.; Plessi, L. Tetrahedron Lett. 1985, 26, 3369.
    • Kruizinga, W. H.; Strijtveen, B.; Kellogg, R. M. J. Org. Chem. 1981, 46, 4321. Lerchen, H. G.; Kunz, H. Tetrahedron Lett. 1985, 26, 5257. Huffman, J.; Desai, R. Synth. Commun. 1983, 13, 553. Torisawa, Y.; Okabe, H.; Ikegami, S. Chem. Lett. 1984, 1555. For a somewhat different application, see: Keinan, E.; Eren, D. J. Org. Chem. 1986, 51, 3165. Cainelli, G.; Manescalchi, F.; Martelli, G.; Panunzio, M.; Plessi, L. Tetrahedron Lett. 1985, 26, 3369.
    • (1981) J. Org. Chem. , vol.46 , pp. 4321
    • Kruizinga, W.H.1    Strijtveen, B.2    Kellogg, R.M.3
  • 13
    • 37049106785 scopus 로고
    • Potts, K. T.; Cipullo, M. J. Org. Chem. 1982, 47, 3038. Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104,3524. Vogtle, F.; Klieser, B. Synthesis 1982, 294. Dietrich-Buchecker, C. 0.; Sauvage, J. P. Tetrahedron Lett. 1983, 24, 5091. Dietrich-Buchecker, C. O.; Sauvage, J. P.; Kintzinger, J. P. Tetrahedron Lett. 1983, 24, 5095. Dietrich-Buchecker, C. O.; Sauvage, J. P.; Kern, J. M. J. Am. Chem. Soc. 1984, 106, 3043. Sauvage, J. P.; Weiss, J. J. Am. Chem. Soc. 1985, 107,6108. Weber, E.; Josel, H. P.; Puff, H.; Franken, S. J. Org. Chem. 1985, 50, 3125. Vogtle, F.; Klieser, B. Synthesis 1982, 294. Vogtle, F.; Bockmann, K. Chem. Ber. 1981, 114, 1048. (1) Klieser, B.; Vogtle, F. Angew. Chem. 1982, 94, 632. Vogtle, F.; Meurer, K.; Mannschreck, Chem. Commun.
    • Barbier, M. J. Chem. Soc., Chem. Commun. 1982, 668. Potts, K. T.; Cipullo, M. J. Org. Chem. 1982, 47, 3038. Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104,3524. Vogtle, F.; Klieser, B. Synthesis 1982, 294. Dietrich-Buchecker, C. 0.; Sauvage, J. P. Tetrahedron Lett. 1983, 24, 5091. Dietrich-Buchecker, C. O.; Sauvage, J. P.; Kintzinger, J. P. Tetrahedron Lett. 1983, 24, 5095. Dietrich-Buchecker, C. O.; Sauvage, J. P.; Kern, J. M. J. Am. Chem. Soc. 1984, 106, 3043. Sauvage, J. P.; Weiss, J. J. Am. Chem. Soc. 1985, 107,6108. Weber, E.; Josel, H. P.; Puff, H.; Franken, S. J. Org. Chem. 1985, 50, 3125. Vogtle, F.; Klieser, B. Synthesis 1982, 294. Vogtle, F.; Bockmann, K. Chem. Ber. 1981, 114, 1048. (1) Klieser, B.; Vogtle, F. Angew. Chem. 1982, 94, 632. Vogtle, F.; Meurer, K.; Mannschreck, A.; Stuhler, G.; Puff, H.; Roloff, A.; Sievers, R. Chem. Ber. 1983, 126,2630. Cram, D. J.; Kasbach, S.; Kim, V. H.; Baczynsky Kalleymeyn, G. W. J. Am. Chem. Soc. 1985, 107,2575. Weber, E. Chem. Ber. 1985, 118,4439. Kissener, W.; Vogtle, F. Angew. Chem. 1985, 97, 782. Roesky, H. W.; Schmidt, H. G. Angew. Chem. 1985, 97, 711. Diederich, F.; Dick, K.; Griebel, D. Chem. Ber. 1985, 3588; Petti, M. A.; Shepodd, T. J.; Dougherty. D. A. Tetrahedron Lett. 1986. 27. 807.
    • (1982) J. Chem. Soc. , pp. 668
    • Barbier, M.1
  • 14
    • 0001058344 scopus 로고
    • Van der Ley, M.; Oosterink, H. J.; Hall, R. H.; Reinhoudt, D. N. Tetrahedron 1981, 37, 3661. Czech, B.; Czech, A.; Bartsch, R. J. Heterocycl. Chem. 1985, 22, 1297.
    • Reinhoudt, D. N.; De Jong, F.; Thomassen, H. P. M. Tetrahedron Lett. 1979, 2067. Van der Ley, M.; Oosterink, H. J.; Hall, R. H.; Reinhoudt, D. N. Tetrahedron 1981, 37, 3661. Czech, B.; Czech, A.; Bartsch, R. J. Heterocycl. Chem. 1985, 22, 1297.
    • (1979) Tetrahedron Lett. , pp. 2067
    • Reinhoudt, D.N.1    De Jong, F.2    Thomassen, H.P.M.3
  • 15
    • 85082935857 scopus 로고
    • General review application of metal fluorides in organic synthesis
    • General review application of metal fluorides in organic synthesis: Yakobson, G. G.; Akhmetova, N. E. Synthesis 1983, 169.
    • (1983) Synthesis , pp. 169
    • Yakobson, G.G.1    Akhmetova, N.E.2
  • 16
  • 17
    • 0021098266 scopus 로고
    • Galli, C.; Mandolini, L. J. Chem. Soc., Perkin Trans. 2 1984, 1435. Mandolini, L.; Masai, B. J. Am. Chem. Soc. 1984, 106, 168.
    • Illuminati, G.; Mandolini, L.; Masai, B. J. Am. Chem. Soc. 1983, 105, 555. Galli, C.; Mandolini, L. J. Chem. Soc., Perkin Trans. 2 1984, 1435. Mandolini, L.; Masai, B. J. Am. Chem. Soc. 1984, 106, 168.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 555
    • Illuminati, G.1    Mandolini, L.2    Masai, B.3
  • 18
    • 0004250303 scopus 로고
    • In The Chemistry of Alkenes
    • General discussion: New York, See also: Hojo, K.; Yoshino, H.; Mukaiyama, T. Chem. Lett. 1977, 437. See also the literature cited in ref,10a and 11.
    • General discussion: Saunders, W. H., Jr. In The Chemistry of Alkenes; Interscience: New York, 1964; pp 149–201. See also: Hojo, K.; Yoshino, H.; Mukaiyama, T. Chem. Lett. 1977, 437. See also the literature cited in ref,10a and 11.
    • (1964) , pp. 149-201
    • Saunders, W.H.1
  • 19
    • 33947487590 scopus 로고
    • Johnson, C. R.; Phillips, W. G. J. Org. Chem. 1967, 32, 1926. Torssel, K. Acta Chem. Scand. 1967, 21, 1.
    • Pfitzner, K. E.; Moffatt, J. G. J. Am. Chem. Soc. 1965, 87, 5661. Johnson, C. R.; Phillips, W. G. J. Org. Chem. 1967, 32, 1926. Torssel, K. Acta Chem. Scand. 1967, 21, 1.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 5661
    • Pfitzner, K.E.1    Moffatt, J.G.2
  • 20
    • 84943692838 scopus 로고
    • for a general review of the NMR spectroscopy of alkali ions
    • See
    • See, for a general review of the NMR spectroscopy of alkali ions: Popov, A. I. Pure Appl. Chem. 1979, 51, 101.
    • (1979) Pure Appl. Chem. , vol.51 , pp. 101
    • Popov, A.I.1
  • 21
    • 0008214570 scopus 로고
    • For example: Mei, E.; Popov, A. I.; Dye, J. L. J. Am. Chem. Soc. 1977, 99, 941. Kauffmann, E.; Dye, J. L.f Lehn, J. M.; Popov, A. I. J. Am. Chem. Soc. 1980, 102, 2274. Shamsipur, M.; Popov, A. I. J. Am. Chem. Soc. 1979, 101, 4051. Shamsipur, M.; Popov, A. I. Inorg. Chim. Acta 1980, 43, 243. Schmidt, E.; Hourdakis, A.; Popov, A. I. Inorg. Chim. Acta 1981, 52, 91. Khazaeli, S.; Popov, A. I.; Dye, S. L. J. Phys. Chem. 1982, 86, 5018. Khazaeli, S.; Dye, J. L.; Popov, A. I. J. Phys. Chem. 1983, 87, 1830.
    • For example: De Witte, W. J.; Liu, L.; Mei, E.; Dye, J. L. J. Solution Chem. 1977, 6, 337. Mei, E.; Popov, A. I.; Dye, J. L. J. Am. Chem. Soc. 1977, 99, 941. Kauffmann, E.; Dye, J. L.f Lehn, J. M.; Popov, A. I. J. Am. Chem. Soc. 1980, 102, 2274. Shamsipur, M.; Popov, A. I. J. Am. Chem. Soc. 1979, 101, 4051. Shamsipur, M.; Popov, A. I. Inorg. Chim. Acta 1980, 43, 243. Schmidt, E.; Hourdakis, A.; Popov, A. I. Inorg. Chim. Acta 1981, 52, 91. Khazaeli, S.; Popov, A. I.; Dye, S. L. J. Phys. Chem. 1982, 86, 5018. Khazaeli, S.; Dye, J. L.; Popov, A. I. J. Phys. Chem. 1983, 87, 1830.
    • (1977) J. Solution Chem. , vol.6 , pp. 337
    • De Witte, W.J.1    Liu, L.2    Mei, E.3    Dye, J.L.4
  • 23
    • 0003466759 scopus 로고
    • Mechanism in Organic Chemistry
    • See, for example: Wiley-Interscience: London, and subsequent discussion.
    • See, for example: Alder, R. W.; Baker, R.; Brown, J. M. Mechanism in Organic Chemistry, Wiley-Interscience: London, 1971; p 43 and subsequent discussion.
    • (1971) , pp. 43
    • Alder, R.W.1    Baker, R.2    Brown, J.M.3
  • 24
    • 0009175984 scopus 로고
    • Aufklarung von Reaktion-smechanismen
    • See, for example: Georg Thieme Verlag: Stuttgart
    • See, for example: Hoffmann, R. W. Aufklarung von Reaktion-smechanismen; Georg Thieme Verlag: Stuttgart, 1976; pp 226 ff.
    • (1976) , pp. 226
    • Hoffmann, R.W.1
  • 25
    • 84981946672 scopus 로고
    • Some other related examples of cation-anion association on chemical reactivity can be found in: Int. Ed. Engl. Solovyanov, A. A.; Beletskaya, I. P. Russ. Chem. Rev. (Engl. Transl.) 1978, 47, 425. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774.
    • Some other related examples of cation-anion association on chemical reactivity can be found in: Smid, J. Angew. Chem., Int. Ed. Engl. 1972, 11,112. Solovyanov, A. A.; Beletskaya, I. P. Russ. Chem. Rev. (Engl. Transl.) 1978, 47, 425. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774.
    • (1972) Angew. Chem. , vol.11 , pp. 112
    • Smid, J.1


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