Advertisement

The Mechanism of the Barbier Reaction

  • Cornelis Blomberg
Part of the Reactivity and Structure: Concepts in Organic Chemistry book series (REACTIVITY, volume 31)

Abstract

One of the crucial factors in the Barbier reaction, just as in the reaction to form the Grignard reagent, is the interaction between the organo halide and the metal.

Keywords

Grignard Reagent Single Electron Transfer Chemically Induce Dynamic Nuclear Polarization Organic Halide Ketyl Radical 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. la.
    Horn E, Polanyi M and Style DWG (1934) Trans Farad Soc 30: 189CrossRefGoogle Scholar
  2. lb.
    Warhurst E (1951) Quart Rev (London) 5: 44CrossRefGoogle Scholar
  3. 2.
    Skell PhS and Doerr RG (1967) J Amer Chem Soc 89: 4688CrossRefGoogle Scholar
  4. 3.
    Skell PhS, Wescott Jr LD, Golstein J-P and Engel RR (1965) J Amer Chem Soc 87: 2829CrossRefGoogle Scholar
  5. 4.
    Timms PL, J Chem Comm 1968: 1525Google Scholar
  6. 5.
    Skell PhS and Girard JE (1972) J Amer Chem Soc 94: 5518CrossRefGoogle Scholar
  7. 6.
    Klabunde KJ, Key MS and Low JYF (1972) J Amer Chem Soc 94: 999CrossRefGoogle Scholar
  8. 7.
    Klabunde KJ, Low JYF and Key MS (1972–1973) J Fluor Chem 2: 207Google Scholar
  9. 8.
    Klabunde KJ (1975) Acc Chem Res 8: 393CrossRefGoogle Scholar
  10. 9.
    Wescott Jr LD, Williford C, Parks F, Dowling M, Sublett S and Klabunde KJ (1976) J Amer Chem Soc 98: 7852CrossRefGoogle Scholar
  11. 10.
    e.g. Ternay Jr AL (1976) Contemporary Organic Chemistry, Saunders WB Company, 2nd edn, p 680Google Scholar
  12. 11.
    Ault BS (1980) J Amer Chem Soc 102: 3480CrossRefGoogle Scholar
  13. 12.
    Tanaka Y, Davis SC and Klabunde KJ (1982) J Amer Chem Soc 104: 1013CrossRefGoogle Scholar
  14. 13.
    Imizu Y and Klabunde KJ (1984) Inorg Chem 23: 3602CrossRefGoogle Scholar
  15. 14.
    Jasien PG and Dykstra CE (1983) J Amer Chem Soc 105: 2089CrossRefGoogle Scholar
  16. 15.
    Klabunde KJ and Whetten A (1986) J Amer Chem Soc 108: 6529CrossRefGoogle Scholar
  17. 16.
    Nuzzo RG and Dubois LH (1986) J Amer Chem Soc 108: 2881CrossRefGoogle Scholar
  18. 17.
    Squire DW, Dulcey CS and Lin MC (1985) Chem Phys Lett 116: 525CrossRefGoogle Scholar
  19. 18.
    Bent BE, Nuzzo RG, Zegarski BR and Dubois LH (1991) J Amer Chem Soc 113: 1137CrossRefGoogle Scholar
  20. 19.
    Bent BE, Nuzzo RG, Zegarski BR and Dubois LH (1991) J Amer Chem Soc 113: 1143CrossRefGoogle Scholar
  21. 20.
    Courtot Ch (1926) Le Magnésium en Chimie Organique, Lorraine-Rigot et Cie, NancyGoogle Scholar
  22. 21.
    Gomberg M and Bachmann WE (1927) J Amer Chem Soc 49: 236CrossRefGoogle Scholar
  23. 22.
    Kharasch MS and Reinmuth O (1954) Grignard Reactions of Non-Metallic Substances. Prentice Hall, New York. p. 61Google Scholar
  24. 23.
    Bryce-Smith D and Cox GF, J Chem Soc 1958: 1050Google Scholar
  25. 24.
    Riichardt C and Trautwein H (1962) Chem Ber 95: 1197CrossRefGoogle Scholar
  26. 25.
    Anteunis M and van Schonte J (1963) Bull Soc Chim Belg 72: 787CrossRefGoogle Scholar
  27. 26.
    Prévost Ch, Gaudemar M, Miginiac L, Bardone-Gaudemar F and Andrac M, Bull Soc Chim France 1959: 769Google Scholar
  28. 27.
    Walborsky HM and Young AE (1964) J Amer Chem Soc 86: 3288CrossRefGoogle Scholar
  29. 28.
    Schwartz AM and Johnson JR (1931) J Amer Chem Soc 53: 1063CrossRefGoogle Scholar
  30. 29.
    Porter CW (1935) J Amer Chem Soc 57: 1436CrossRefGoogle Scholar
  31. 30.
    Tarbell DS and Weiss M (1939) J Amer Chem Soc 61: 1203CrossRefGoogle Scholar
  32. 31.
    Walborsky HM and Young AE (1961) J Amer Chem Soc 83: 2595 (1961)Google Scholar
  33. 32.
    Walborsky HM, Impastato FJ and Young AE (1964) J Amer Chem Soc 86: 3283 and references cited therein.Google Scholar
  34. 33.
    Walborsky HM, Chen C-J and Webb JL, Tetrahedron Lett 1964: 3551Google Scholar
  35. 34.
    Walborsky HM and Chen C-J (1971) J Amer Chem Soc 93: 671CrossRefGoogle Scholar
  36. 35.
    Walborsky HM and Aronoff MS (1973) J Organometal Chem 51: 31CrossRefGoogle Scholar
  37. 36.
    Walborsky HM and Banks RB (1980) Bull Soc Chim Belg 89: 849CrossRefGoogle Scholar
  38. 37.
    Walborsky HM and Aronoff MJ (1965) J Organometal Chem 4: 418CrossRefGoogle Scholar
  39. 38.
    Bodewitz HWHJ, Blomberg C and Bickelhaupt F, Tetrahedron Lett 1972: 281Google Scholar
  40. 39.
    Closs GL (1969) J Amer Chem Soc 91: 4552CrossRefGoogle Scholar
  41. 40.
    Kaptein R and Oosterhoff LJ (1969) Chem Phys Lett 4: 214CrossRefGoogle Scholar
  42. 41.
    Bodewitz HWHJ, Blomberg C and Bickelhaupt F (1973) Tetrahedron 27: 719CrossRefGoogle Scholar
  43. 42.
    Bodewitz HWHJ, Blomberg C and Bickelhaupt F (1975) Tetrahedron 31: 1053CrossRefGoogle Scholar
  44. 43.
    Bodewitz HWHJ, Blomberg C and Bickelhaupt F, Tetrahedron Lett 1975: 2003Google Scholar
  45. 44.
    Schaart BJ, Bodewitz HWHJ, Blomberg C and Bickelhaupt F (1976) J Amer Chem Soc 98: 3712CrossRefGoogle Scholar
  46. 45.
    Bodewitz HWHJ, Schaart BJ, van der Niet JD, Blomberg C, Bickelhaupt F and den Hollander JA (1978) Tetrahedron 34: 2523CrossRefGoogle Scholar
  47. 46.
    Schaart BJ, Blomberg C, Akkerman OS and Bickelhaupt F (1980) Canad J Chem 58: 932CrossRefGoogle Scholar
  48. 47.
    Dubois JE, Bauer P, Molle G and Daza J (1977) Compt Rend Sér C 284: 145Google Scholar
  49. 48.
    Dubois JE, Molle G, Tourillon G and Bauer P (1979) Tetrahedron Lett 20: 5069CrossRefGoogle Scholar
  50. 49.
    Molle G, Bauer P and Dubois JE (1982) J Org Chem 47: 4120CrossRefGoogle Scholar
  51. 50.
    Molle G, Dubois JE and Bauer P (1978) Synth Comm 8: 39CrossRefGoogle Scholar
  52. 51.
    Molle G, Dubois JE and Bauer P (1978) Tetrahedron Lett 19: 3177CrossRefGoogle Scholar
  53. 52.
    Bauer P and Molle G (1978) Tetrahedron Lett. 19: 4853CrossRefGoogle Scholar
  54. 53.
    Molle G and Bauer P (1982) J Amer Chem Soc 104: 3481CrossRefGoogle Scholar
  55. 54.
    Molle G, Bauer P and Dubois JE (1983) J Org Chem 48: 2975CrossRefGoogle Scholar
  56. 55.
    Dubois JE, Bauer P and Kaddani B (1985) Tetrahedron Lett 26: 57CrossRefGoogle Scholar
  57. 56.
    Dubois JE, Bauer P and Briand S (1988) Tetrahedron Lett 29: 3935CrossRefGoogle Scholar
  58. 57.
    Rogers HR, Hill CL, Fujiwara Y, Rogers RJ, Mitchell HL and Whitesides GM (1980) J Amer Chem Soc 102: 217CrossRefGoogle Scholar
  59. 58.
    Rogers HR, Deutch J and Whitesides GM (1980) J Amer Chem Soc 102: 226CrossRefGoogle Scholar
  60. 59.
    Rogers HR, Rogers RJ, Mitchell HL and Whitesides GM (1980) J Amer Chem Soc 102: 231CrossRefGoogle Scholar
  61. 60.
    Barber JJ and Whitesides GM (1980) J Amer Chem Soc 102: 239CrossRefGoogle Scholar
  62. 61.
    Root KS, Deutch J and Whitesides GM (1981) J Amer Chem Soc 103: 5475CrossRefGoogle Scholar
  63. 62.
    Lawrence LM and Whitesides GM (1980) J Amer Chem Soc 102: 2493CrossRefGoogle Scholar
  64. 63.
    Garst JF, Deutch JE and Whitesides GM (1986) J Amer Chem Soc 108: 2490CrossRefGoogle Scholar
  65. 64.
    Ashby EC and Oswald J (1988) J Org Chem 53: 6068CrossRefGoogle Scholar
  66. 65.
    Walborsky HM and Zimmermann C (1992) J Amer Chem Soc 114: 4996CrossRefGoogle Scholar
  67. 66.
    Garst JF, Ungvary F, Batlaw R and Lawrence EL (1991) J Amer Chem Soc 113: 5392CrossRefGoogle Scholar
  68. 67a.
    Walborsky HM and Rachon J (1989) J Amer Chem Soc 111: 1896CrossRefGoogle Scholar
  69. 67b.
    Rachin J and Walborsky HM (1989) Tetrahedron Lett 30: 7345CrossRefGoogle Scholar
  70. 67c.
    Walborsky HM (1990) Acc Chem Res 23: 286CrossRefGoogle Scholar
  71. 68.
    Crandall JK and Magaha HS (1982) J Org Chem 47: 5368CrossRefGoogle Scholar
  72. 69.
    Cameron GG and Milton AJS, J Chem Soc Perkin Trans. II, 1976: 378Google Scholar
  73. 70.
    Killinger TA, Boughton NA, Runge TA and Wolinsky J (1977) J Organometal Chem 124: 131CrossRefGoogle Scholar
  74. 71.
    Pearce PJ, Richards DH and Scilly NF, J Chem Soc D 1970: 1160Google Scholar
  75. 72.
    Pearce PJ, Richards DH and Scilly NF, J Chem Soc Perkin Trans I 1972: 1655Google Scholar
  76. 73.
    Pearce PJ, Richards DH and Scilly NF (1974) British Patent 1335, 1975, 140. Chem Abstr 80: 70306Google Scholar
  77. 74.
    Garst JF and Smith CD (1976) J Amer Chem Soc 98: 1520CrossRefGoogle Scholar
  78. 75.
    Bryce-Smith D and Wakefield BJ, Tetrahedron Lett 1964: 3295Google Scholar
  79. 76.
    Blomberg C and Mosher HS (1968) J Organometall Chem 13: 519CrossRefGoogle Scholar
  80. 77.
    Ashby EC, Buhler JD, Lopp IG, Wieseman TL, Bowers Jr JC and Laemrnle JT (1976) J Amer Chem Soc 98: 6561CrossRefGoogle Scholar
  81. 78.
    Okubo M (1977) Bull Chem Soc Japan 50: 2379CrossRefGoogle Scholar
  82. 79.
    Hartog FA (1978) Thesis Free University Amsterdam Available on request.Google Scholar
  83. 80.
    Ashby EC and Goel AB (1977) J Amer Chem Soc 99: 310CrossRefGoogle Scholar
  84. 81.
    Givelet MHE (1968) Compt Rend Sér C 278: 881Google Scholar
  85. 82.
    Givelet MHE (1969) French Patent 1541058, (1968); Chem Abstr 70: 25265yGoogle Scholar
  86. 83.
    Fuson RC, Armstrong MD and Speck SB (1942) J Org Chem 7: 297CrossRefGoogle Scholar
  87. 84.
    Holm T and Crossland I (1971) Acta Chem Scand 25: 56Google Scholar
  88. 85.
    Ashby EC, Laemmle JT and Neumann HM (1974) Acc Chem Res 7: 272CrossRefGoogle Scholar
  89. 86.
    Ashby EC and Laemmle JT (1975) Chem Rev 75: 521CrossRefGoogle Scholar
  90. 87.
    Katzenellengbogen JA and Lenox RS (1973) J Org Chem 38: 326CrossRefGoogle Scholar
  91. 88.
    Blancou H, Morreau P and Commeyras A, J Chem Soc Chem Comm 1976: 885Google Scholar
  92. 89.
    Boldrini GP, Savoia D, Tagliavini A, Trombini C and Umani-Ronchi A (1983) J Org Chem 48: 4108CrossRefGoogle Scholar
  93. 90.
    Uneyama K, Matsuda H and Torii S (1984) Tetrahedron Lett 25: 6017CrossRefGoogle Scholar
  94. 91.
    de Souza-Barbosa JC, Luche J-L and Pétrier C (1987) Tetrahedron Lett 28: 2013CrossRefGoogle Scholar
  95. 92.
    de Souza-Barboza JC, Pétrier C and Luche J-L (1988) J Org Chem 53: 1212CrossRefGoogle Scholar
  96. 93.
    Moyano A, Pericàs MA, Riera A and Luche J-L (1990) Tetrahedron Lett 31: 7619CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1993

Authors and Affiliations

  • Cornelis Blomberg
    • 1
  1. 1.AbcoudeThe Netherlands

Personalised recommendations