The Electron-Releasing Carbonyl Group. Part I: Discovery And Theoretical Studies

Chimica Oggi

Volumn 15, Issue 1-2, 1997, Pages 18-25

  Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

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EID: 0031482620     PISSN: 0392839X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (76)

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47. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
48. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
49. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
50. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
51. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
52. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
53. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
54. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
55. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
56. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
57. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
58. See e.g.: G. Klopman; J. Am. Chem. Soc. 90 223 (1968) L. Salem; ibidem 90 543, 553 (1968) K. Fukui; Acc. Chem. Res. 4 57 (1971) and Bull. Chem. Soc. Jpn. 39 498 (1966) I. Fleming; in: Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976 R. Sustmann; Pure Appl. Chem. 40 569 (1974) W.C. Herndon; Chem. Rev. 72 57 (1972) R.F. Hudson; Angew. Chem., Int. Ed. Engl 12 36 (1973) N.D. Epiotis; J. Am. Chem. Soc. 95 5624 (1973) K.N. Houk; Acc. Chem. Res. 8 361 (1975) O. Eisenstein, J.M. Lefour, N.T. Anh, R.F. Hudson; Tetrahedron 33 523 (1977) P.V. Alston, R.N. Ottenbrite, J. Newby; J. Org. Chem. 44 4939 (1979) M. J.S. Dewar, R.C. Dougherty; in: The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975
59. M. Avenati, P.-A. Carrupt, D. Quarroz, P. Vogel; Helv. Chim. Acta 65 188 (1982)
60. A. Chollet, C. Mahaim, C. Foctisch, M. Hardy, P. Vogel; Helv. Chim. Acta 60 59 (1977)
61. R. B. Woodward, T. J. Katz; Tetrahedron 5 70 (1979) N.D. Epiotis; Theory of Organic Reactions, Springer Verlag, Berlin, 1978, Chap. 6 M.J.S. Dewar, A.B. Pierini; J. Am. Chem. Soc. 106 203 (1984) M.J.S. Dewar; ibidem 106 209 (1984) M.J.S. Dewar, S. Olivella, J.J.P. Stewart; ibidem 108 5771 (1986) See also: R.A. Firestone; J. Org. Chem. 33 2285 (1968) and Tetrahedron 33 3009 (1977) J. Cossy, P.-A. Carrupt, P. Vogel; in: The Chemistry of Double-bonded Functional Group, Supplement, A.S. Patai Ed.; J. Wiley & Sons, 1989, Chap. 18
62. R. B. Woodward, T. J. Katz; Tetrahedron 5 70 (1979) N.D. Epiotis; Theory of Organic Reactions, Springer Verlag, Berlin, 1978, Chap. 6 M.J.S. Dewar, A.B. Pierini; J. Am. Chem. Soc. 106 203 (1984) M.J.S. Dewar; ibidem 106 209 (1984) M.J.S. Dewar, S. Olivella, J.J.P. Stewart; ibidem 108 5771 (1986) See also: R.A. Firestone; J. Org. Chem. 33 2285 (1968) and Tetrahedron 33 3009 (1977) J. Cossy, P.-A. Carrupt, P. Vogel; in: The Chemistry of Double-bonded Functional Group, Supplement, A.S. Patai Ed.; J. Wiley & Sons, 1989, Chap. 18
63. R. B. Woodward, T. J. Katz; Tetrahedron 5 70 (1979) N.D. Epiotis; Theory of Organic Reactions, Springer Verlag, Berlin, 1978, Chap. 6 M.J.S. Dewar, A.B. Pierini; J. Am. Chem. Soc. 106 203 (1984) M.J.S. Dewar; ibidem 106 209 (1984) M.J.S. Dewar, S. Olivella, J.J.P. Stewart; ibidem 108 5771 (1986) See also: R.A. Firestone; J. Org. Chem. 33 2285 (1968) and Tetrahedron 33 3009 (1977) J. Cossy, P.-A. Carrupt, P. Vogel; in: The Chemistry of Double-bonded Functional Group, Supplement, A.S. Patai Ed.; J. Wiley & Sons, 1989, Chap. 18
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