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Volumn 2004, Issue 9, 2004, Pages 19-33

Some new observations on an old reaction: Disproportionation and the formation of P-O-P intermediates in the Michaelis-Arbuzov reaction of triaryl phosphites with alkyl halides

Author keywords

Disproportionation; Michaelis Arbuzov; NMR spectroscopy; Quasiphosphonium

Indexed keywords

ALKYL GROUP; ARGON; BROMINE; HALIDE; IODINE; METHYL GROUP; OXYGEN; PHOSPHITE;

EID: 5644285666     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (11)

References (41)
  • 1
    • 0001588748 scopus 로고
    • Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307. Harvey, R. G.; De Sombre, E. R. The Michaelis-Arbuzov and Related Reactions, in Topics in Phosphorus Chemistry, eds. Grayson, M.; Griffith, E. J. Wiley, New York, 1964, 1, 57. Hudson, R. F. Structure and Mechanism in Organophosphorus Chemistry, Academic Press, London, 1965. Kirby, A. J.; Warren, S. G. The Organic Chemistry of Phosphorus, Elsevier, New York, 1967.
    • (1964) Pure Appl. Chem. , vol.9 , pp. 307
    • Arbuzov, B.A.1
  • 2
    • 0002242273 scopus 로고
    • The Michaelis-Arbuzov and related reactions
    • eds. Grayson, M.; Griffith, E. J. Wiley, New York
    • Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307. Harvey, R. G.; De Sombre, E. R. The Michaelis-Arbuzov and Related Reactions, in Topics in Phosphorus Chemistry, eds. Grayson, M.; Griffith, E. J. Wiley, New York, 1964, 1, 57. Hudson, R. F. Structure and Mechanism in Organophosphorus Chemistry, Academic Press, London, 1965. Kirby, A. J.; Warren, S. G. The Organic Chemistry of Phosphorus, Elsevier, New York, 1967.
    • (1964) Topics in Phosphorus Chemistry , vol.1 , pp. 57
    • Harvey, R.G.1    De Sombre, E.R.2
  • 3
    • 0003532918 scopus 로고
    • Academic Press, London
    • Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307. Harvey, R. G.; De Sombre, E. R. The Michaelis-Arbuzov and Related Reactions, in Topics in Phosphorus Chemistry, eds. Grayson, M.; Griffith, E. J. Wiley, New York, 1964, 1, 57. Hudson, R. F. Structure and Mechanism in Organophosphorus Chemistry, Academic Press, London, 1965. Kirby, A. J.; Warren, S. G. The Organic Chemistry of Phosphorus, Elsevier, New York, 1967.
    • (1965) Structure and Mechanism in Organophosphorus Chemistry
    • Hudson, R.F.1
  • 4
    • 0003792184 scopus 로고
    • Elsevier, New York
    • Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307. Harvey, R. G.; De Sombre, E. R. The Michaelis-Arbuzov and Related Reactions, in Topics in Phosphorus Chemistry, eds. Grayson, M.; Griffith, E. J. Wiley, New York, 1964, 1, 57. Hudson, R. F. Structure and Mechanism in Organophosphorus Chemistry, Academic Press, London, 1965. Kirby, A. J.; Warren, S. G. The Organic Chemistry of Phosphorus, Elsevier, New York, 1967.
    • (1967) The Organic Chemistry of Phosphorus
    • Kirby, A.J.1    Warren, S.G.2
  • 5
    • 5644290819 scopus 로고
    • Wiley, New York
    • Kosolapoff, G. M.; MaierL. eds. Organic Phosphorus Compounds, Wiley, New York, 1972, vol. 3, pp. 360-365; 1973 vol. 5, pp. 70-71; 1973, vol. 6, pp. 14-17; 1976, vol. 7, pp. 23-27. Hartley, F. R. ed. The Chemistry of Organophosphorus Compounds, Wiley, Chichester, 1992, vol. 2, pp. 208-212; 1996, vol. 4, pp. 50-69, 149-159, 320-329.
    • (1972) Organic Phosphorus Compounds , vol.3 , pp. 360-365
    • Kosolapoff, G.M.1    Maier, L.2
  • 6
    • 5644255784 scopus 로고
    • Kosolapoff, G. M.; MaierL. eds. Organic Phosphorus Compounds, Wiley, New York, 1972, vol. 3, pp. 360-365; 1973 vol. 5, pp. 70-71; 1973, vol. 6, pp. 14-17; 1976, vol. 7, pp. 23-27. Hartley, F. R. ed. The Chemistry of Organophosphorus Compounds, Wiley, Chichester, 1992, vol. 2, pp. 208-212; 1996, vol. 4, pp. 50-69, 149-159, 320-329.
    • (1973) Organic Phosphorus Compounds , vol.5 , pp. 70-71
  • 7
    • 5644228830 scopus 로고
    • Kosolapoff, G. M.; MaierL. eds. Organic Phosphorus Compounds, Wiley, New York, 1972, vol. 3, pp. 360-365; 1973 vol. 5, pp. 70-71; 1973, vol. 6, pp. 14-17; 1976, vol. 7, pp. 23-27. Hartley, F. R. ed. The Chemistry of Organophosphorus Compounds, Wiley, Chichester, 1992, vol. 2, pp. 208-212; 1996, vol. 4, pp. 50-69, 149-159, 320-329.
    • (1973) Organic Phosphorus Compounds , vol.6 , pp. 14-17
  • 8
    • 0003607090 scopus 로고
    • Kosolapoff, G. M.; MaierL. eds. Organic Phosphorus Compounds, Wiley, New York, 1972, vol. 3, pp. 360-365; 1973 vol. 5, pp. 70-71; 1973, vol. 6, pp. 14-17; 1976, vol. 7, pp. 23-27. Hartley, F. R. ed. The Chemistry of Organophosphorus Compounds, Wiley, Chichester, 1992, vol. 2, pp. 208-212; 1996, vol. 4, pp. 50-69, 149-159, 320-329.
    • (1976) Organic Phosphorus Compounds , vol.7 , pp. 23-27
  • 9
    • 5644257099 scopus 로고
    • Wiley, Chichester
    • Kosolapoff, G. M.; MaierL. eds. Organic Phosphorus Compounds, Wiley, New York, 1972, vol. 3, pp. 360-365; 1973 vol. 5, pp. 70-71; 1973, vol. 6, pp. 14-17; 1976, vol. 7, pp. 23-27. Hartley, F. R. ed. The Chemistry of Organophosphorus Compounds, Wiley, Chichester, 1992, vol. 2, pp. 208-212; 1996, vol. 4, pp. 50-69, 149-159, 320-329.
    • (1992) The Chemistry of Organophosphorus Compounds , vol.2 , pp. 208-212
    • Hartley, F.R.1
  • 10
    • 5644298820 scopus 로고    scopus 로고
    • Kosolapoff, G. M.; MaierL. eds. Organic Phosphorus Compounds, Wiley, New York, 1972, vol. 3, pp. 360-365; 1973 vol. 5, pp. 70-71; 1973, vol. 6, pp. 14-17; 1976, vol. 7, pp. 23-27. Hartley, F. R. ed. The Chemistry of Organophosphorus Compounds, Wiley, Chichester, 1992, vol. 2, pp. 208-212; 1996, vol. 4, pp. 50-69, 149-159, 320-329.
    • (1996) The Chemistry of Organophosphorus Compounds , vol.4 , pp. 50-69
  • 12
    • 37849036602 scopus 로고
    • Michaelis, A.; Kaehne, R. Berichte 1898, 31, 1048. Arbuzov, A. E. J. Russ. Phys. Chem. Soc. 1906, 38, 687. Landauer, S. R.; Rydon, H. N. Chem and Ind. 1951, 313. Landauer, S. R.; Rydon, H. N. J. Chem. Soc. 1953, 2224.
    • (1898) Berichte , vol.31 , pp. 1048
    • Michaelis, A.1    Kaehne, R.2
  • 13
    • 0000555750 scopus 로고
    • Michaelis, A.; Kaehne, R. Berichte 1898, 31, 1048. Arbuzov, A. E. J. Russ. Phys. Chem. Soc. 1906, 38, 687. Landauer, S. R.; Rydon, H. N. Chem and Ind. 1951, 313. Landauer, S. R.; Rydon, H. N. J. Chem. Soc. 1953, 2224.
    • (1906) J. Russ. Phys. Chem. Soc. , vol.38 , pp. 687
    • Arbuzov, A.E.1
  • 14
    • 5644235148 scopus 로고
    • Michaelis, A.; Kaehne, R. Berichte 1898, 31, 1048. Arbuzov, A. E. J. Russ. Phys. Chem. Soc. 1906, 38, 687. Landauer, S. R.; Rydon, H. N. Chem and Ind. 1951, 313. Landauer, S. R.; Rydon, H. N. J. Chem. Soc. 1953, 2224.
    • (1951) Chem. and Ind. , pp. 313
    • Landauer, S.R.1    Rydon, H.N.2
  • 15
    • 37049158301 scopus 로고
    • Michaelis, A.; Kaehne, R. Berichte 1898, 31, 1048. Arbuzov, A. E. J. Russ. Phys. Chem. Soc. 1906, 38, 687. Landauer, S. R.; Rydon, H. N. Chem and Ind. 1951, 313. Landauer, S. R.; Rydon, H. N. J. Chem. Soc. 1953, 2224.
    • (1953) J. Chem. Soc. , pp. 2224
    • Landauer, S.R.1    Rydon, H.N.2
  • 18
    • 37049109850 scopus 로고
    • Henrick, K.; Hudson, H. R.; Kow, A. Chem. Commun. 1980, 226. Petneházy, I.; Szakál, Gy.; Toke, L.; Hudson, H. R.; Powroznyk, L.; Cooksey, C. J. Tetrahedron 1983, 24, 4229. Henrick, K.; Hudson, H. R.; McPartlin, M.; Powroznik, L.; Shaw, L. S. J. Organometal. Chem. 1992, 437, 157. Hudson, H. R.; Matthews, R. W.; McPartlin, M.; Pryce, M. A.; Shode, O. O. J. Chem. Soc., Perkin Trans. 2 1993, 1433. Imre, C.; Modro, T. A.; van Rooyen, P. H.; Wagener, C. C. P.; Wallace, K.; Hudson, H. R.; McPartlin, M.; Nasirun, J. B.; Powroznyk, L. J. Phys. Org. Chem., 1995, 8, 41.
    • (1980) Chem. Commun. , pp. 226
    • Henrick, K.1    Hudson, H.R.2    Kow, A.3
  • 19
    • 0001366669 scopus 로고
    • Henrick, K.; Hudson, H. R.; Kow, A. Chem. Commun. 1980, 226. Petneházy, I.; Szakál, Gy.; Toke, L.; Hudson, H. R.; Powroznyk, L.; Cooksey, C. J. Tetrahedron 1983, 24, 4229. Henrick, K.; Hudson, H. R.; McPartlin, M.; Powroznik, L.; Shaw, L. S. J. Organometal. Chem. 1992, 437, 157. Hudson, H. R.; Matthews, R. W.; McPartlin, M.; Pryce, M. A.; Shode, O. O. J. Chem. Soc., Perkin Trans. 2 1993, 1433. Imre, C.; Modro, T. A.; van Rooyen, P. H.; Wagener, C. C. P.; Wallace, K.; Hudson, H. R.; McPartlin, M.; Nasirun, J. B.; Powroznyk, L. J. Phys. Org. Chem., 1995, 8, 41.
    • (1983) Tetrahedron , vol.24 , pp. 4229
    • Petneházy, I.1    Szakál, Gy.2    Toke, L.3    Hudson, H.R.4    Powroznyk, L.5    Cooksey, C.J.6
  • 20
    • 0342728568 scopus 로고
    • Henrick, K.; Hudson, H. R.; Kow, A. Chem. Commun. 1980, 226. Petneházy, I.; Szakál, Gy.; Toke, L.; Hudson, H. R.; Powroznyk, L.; Cooksey, C. J. Tetrahedron 1983, 24, 4229. Henrick, K.; Hudson, H. R.; McPartlin, M.; Powroznik, L.; Shaw, L. S. J. Organometal. Chem. 1992, 437, 157. Hudson, H. R.; Matthews, R. W.; McPartlin, M.; Pryce, M. A.; Shode, O. O. J. Chem. Soc., Perkin Trans. 2 1993, 1433. Imre, C.; Modro, T. A.; van Rooyen, P. H.; Wagener, C. C. P.; Wallace, K.; Hudson, H. R.; McPartlin, M.; Nasirun, J. B.; Powroznyk, L. J. Phys. Org. Chem., 1995, 8, 41.
    • (1992) J. Organometal. Chem. , vol.437 , pp. 157
    • Henrick, K.1    Hudson, H.R.2    McPartlin, M.3    Powroznik, L.4    Shaw, L.S.5
  • 21
    • 37049074422 scopus 로고
    • Henrick, K.; Hudson, H. R.; Kow, A. Chem. Commun. 1980, 226. Petneházy, I.; Szakál, Gy.; Toke, L.; Hudson, H. R.; Powroznyk, L.; Cooksey, C. J. Tetrahedron 1983, 24, 4229. Henrick, K.; Hudson, H. R.; McPartlin, M.; Powroznik, L.; Shaw, L. S. J. Organometal. Chem. 1992, 437, 157. Hudson, H. R.; Matthews, R. W.; McPartlin, M.; Pryce, M. A.; Shode, O. O. J. Chem. Soc., Perkin Trans. 2 1993, 1433. Imre, C.; Modro, T. A.; van Rooyen, P. H.; Wagener, C. C. P.; Wallace, K.; Hudson, H. R.; McPartlin, M.; Nasirun, J. B.; Powroznyk, L. J. Phys. Org. Chem., 1995, 8, 41.
    • (1993) J. Chem. Soc., Perkin Trans. 2 , pp. 1433
    • Hudson, H.R.1    Matthews, R.W.2    McPartlin, M.3    Pryce, M.A.4    Shode, O.O.5
  • 22
    • 0344135051 scopus 로고
    • Henrick, K.; Hudson, H. R.; Kow, A. Chem. Commun. 1980, 226. Petneházy, I.; Szakál, Gy.; Toke, L.; Hudson, H. R.; Powroznyk, L.; Cooksey, C. J. Tetrahedron 1983, 24, 4229. Henrick, K.; Hudson, H. R.; McPartlin, M.; Powroznik, L.; Shaw, L. S. J. Organometal. Chem. 1992, 437, 157. Hudson, H. R.; Matthews, R. W.; McPartlin, M.; Pryce, M. A.; Shode, O. O. J. Chem. Soc., Perkin Trans. 2 1993, 1433. Imre, C.; Modro, T. A.; van Rooyen, P. H.; Wagener, C. C. P.; Wallace, K.; Hudson, H. R.; McPartlin, M.; Nasirun, J. B.; Powroznyk, L. J. Phys. Org. Chem., 1995, 8, 41.
    • (1995) J. Phys. Org. Chem. , vol.8 , pp. 41
    • Imre, C.1    Modro, T.A.2    Van Rooyen, P.H.3    Wagener, C.C.P.4    Wallace, K.5    Hudson, H.R.6    McPartlin, M.7    Nasirun, J.B.8    Powroznyk, L.9
  • 23
    • 5644232191 scopus 로고
    • PhD Thesis (University of London)
    • Weekes, J. E. PhD Thesis (University of London), 1972.
    • (1972)
    • Weekes, J.E.1
  • 25
    • 84913058276 scopus 로고
    • Henrick, K.; Hudson, H. R.; Matthews, R. W.; McPartlin, E. M.; Powroznyk, L.; Shode, O. O. Proc. X Internat. Conf. Phosphorus Chem. Bonn, 31 Aug-6 Sept, 1986, eds. Appel, R.; Knoll, F.; Ruppert, I. Phosphorus and Sulfur 1987, 30, 157.
    • (1987) Phosphorus and Sulfur , vol.30 , pp. 157
  • 29
    • 0347966408 scopus 로고
    • Quasi-phosphonium intermediates and compounds
    • eds. Grayson, M.; Griffith, E. J. Wiley, New York
    • Hudson, H. R. Quasi-Phosphonium Intermediates and Compounds, in Topics in Phosphorus Chemistry, eds. Grayson, M.; Griffith, E. J. Wiley, New York, 1983, 11, 339.
    • (1983) Topics in Phosphorus Chemistry , vol.11 , pp. 339
    • Hudson, H.R.1
  • 32
    • 0002646662 scopus 로고
    • Rydon, H. N.; Tonge, B. L. J. Chem. Soc. 1956, 3043. Sigal, I. S.; Westheimer, F. H.; J. Am. Chem. Soc. 1979, 101, 5329. Sigal, I. S.; Westheimer, F. H. J. Am. Chem. Soc. 1979, 101, 5334.
    • (1956) J. Chem. Soc. , pp. 3043
    • Rydon, H.N.1    Tonge, B.L.2
  • 33
    • 5644258462 scopus 로고
    • Rydon, H. N.; Tonge, B. L. J. Chem. Soc. 1956, 3043. Sigal, I. S.; Westheimer, F. H.; J. Am. Chem. Soc. 1979, 101, 5329. Sigal, I. S.; Westheimer, F. H. J. Am. Chem. Soc. 1979, 101, 5334.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 5329
    • Sigal, I.S.1    Westheimer, F.H.2
  • 34
    • 5644266246 scopus 로고
    • Rydon, H. N.; Tonge, B. L. J. Chem. Soc. 1956, 3043. Sigal, I. S.; Westheimer, F. H.; J. Am. Chem. Soc. 1979, 101, 5329. Sigal, I. S.; Westheimer, F. H. J. Am. Chem. Soc. 1979, 101, 5334.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 5334
    • Sigal, I.S.1    Westheimer, F.H.2
  • 35
    • 0040665481 scopus 로고    scopus 로고
    • Riess, J. G.; Van Wazer, J. R. J. Am. Chem. Soc. 1966, 88, 2166. Crutchfield, M. M.; Dungan, C. H.; Letcher, J. H.; Mark, V.; Van Wazer, J. R. Topics in Phosphorus Chemistry, eds. Grayson, M.; Griffith, E. J. Wiley, New York 1967, 5, 259. Edmundson, R.S. ch. 9 in ref. 12, p.230.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2166
    • Riess, J.G.1    Van Wazer, J.R.2
  • 37
    • 0040665481 scopus 로고    scopus 로고
    • Edmundson, R.S. ch. 9 in ref. 12, p.230
    • Riess, J. G.; Van Wazer, J. R. J. Am. Chem. Soc. 1966, 88, 2166. Crutchfield, M. M.; Dungan, C. H.; Letcher, J. H.; Mark, V.; Van Wazer, J. R. Topics in Phosphorus Chemistry, eds. Grayson, M.; Griffith, E. J. Wiley, New York 1967, 5, 259. Edmundson, R.S. ch. 9 in ref. 12, p.230.
  • 38
    • 5644257100 scopus 로고    scopus 로고
    • note
    • Catalysis of the Michaelis-Arbuzov reaction by phosphonate was recognized many years ago (cf. R. G. Harvey and E. R. De Sombre in ref. 1, p. 76) but the mechanism of catalysis was uncertain. The examples reported were reactions of trialkyl phosphites, for which intermediates had not at that stage been clearly identified.
  • 39
    • 5644254537 scopus 로고
    • Houalla, D.; Wolf, R. Compt. Rend. 1958, 247, 482. Walsh, E. N. J. Am. Chem. Soc. 1959, 81, 3023.
    • (1958) Compt. Rend. , vol.247 , pp. 482
    • Houalla, D.1    Wolf, R.2
  • 40
    • 33748059638 scopus 로고
    • Houalla, D.; Wolf, R. Compt. Rend. 1958, 247, 482. Walsh, E. N. J. Am. Chem. Soc. 1959, 81, 3023.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 3023
    • Walsh, E.N.1
  • 41
    • 1542425012 scopus 로고
    • Organic derivatives of phosphorous and thiophosphorous acid
    • ch. 13, eds. Kosolapoff, G. M.; MaierL. Wiley, New York
    • Gerrard, W.; Hudson, H. R. Organic Derivatives of Phosphorous and Thiophosphorous Acid, ch. 13 in vol. 5 of Organic Phosphorus Compounds, eds. Kosolapoff, G. M.; MaierL. Wiley, New York, 1973, p. 32.
    • (1973) Organic Phosphorus Compounds , vol.5 , pp. 32
    • Gerrard, W.1    Hudson, H.R.2


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