Skip to main content

Part of the book series: Reactivity and Structure: Concepts in Organic Chemistry ((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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 16.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Horn E, Polanyi M and Style DWG (1934) Trans Farad Soc 30: 189

    Article  Google Scholar 

  2. Warhurst E (1951) Quart Rev (London) 5: 44

    Article  CAS  Google Scholar 

  3. Skell PhS and Doerr RG (1967) J Amer Chem Soc 89: 4688

    Article  CAS  Google Scholar 

  4. Skell PhS, Wescott Jr LD, Golstein J-P and Engel RR (1965) J Amer Chem Soc 87: 2829

    Article  CAS  Google Scholar 

  5. Timms PL, J Chem Comm 1968: 1525

    Google Scholar 

  6. Skell PhS and Girard JE (1972) J Amer Chem Soc 94: 5518

    Article  CAS  Google Scholar 

  7. Klabunde KJ, Key MS and Low JYF (1972) J Amer Chem Soc 94: 999

    Article  CAS  Google Scholar 

  8. Klabunde KJ, Low JYF and Key MS (1972–1973) J Fluor Chem 2: 207

    Google Scholar 

  9. Klabunde KJ (1975) Acc Chem Res 8: 393

    Article  CAS  Google Scholar 

  10. Wescott Jr LD, Williford C, Parks F, Dowling M, Sublett S and Klabunde KJ (1976) J Amer Chem Soc 98: 7852

    Article  Google Scholar 

  11. e.g. Ternay Jr AL (1976) Contemporary Organic Chemistry, Saunders WB Company, 2nd edn, p 680

    Google Scholar 

  12. Ault BS (1980) J Amer Chem Soc 102: 3480

    Article  CAS  Google Scholar 

  13. Tanaka Y, Davis SC and Klabunde KJ (1982) J Amer Chem Soc 104: 1013

    Article  CAS  Google Scholar 

  14. Imizu Y and Klabunde KJ (1984) Inorg Chem 23: 3602

    Article  CAS  Google Scholar 

  15. Jasien PG and Dykstra CE (1983) J Amer Chem Soc 105: 2089

    Article  CAS  Google Scholar 

  16. Klabunde KJ and Whetten A (1986) J Amer Chem Soc 108: 6529

    Article  CAS  Google Scholar 

  17. Nuzzo RG and Dubois LH (1986) J Amer Chem Soc 108: 2881

    Article  CAS  Google Scholar 

  18. Squire DW, Dulcey CS and Lin MC (1985) Chem Phys Lett 116: 525

    Article  CAS  Google Scholar 

  19. Bent BE, Nuzzo RG, Zegarski BR and Dubois LH (1991) J Amer Chem Soc 113: 1137

    Article  CAS  Google Scholar 

  20. Bent BE, Nuzzo RG, Zegarski BR and Dubois LH (1991) J Amer Chem Soc 113: 1143

    Article  CAS  Google Scholar 

  21. Courtot Ch (1926) Le Magnésium en Chimie Organique, Lorraine-Rigot et Cie, Nancy

    Google Scholar 

  22. Gomberg M and Bachmann WE (1927) J Amer Chem Soc 49: 236

    Article  CAS  Google Scholar 

  23. Kharasch MS and Reinmuth O (1954) Grignard Reactions of Non-Metallic Substances. Prentice Hall, New York. p. 61

    Google Scholar 

  24. Bryce-Smith D and Cox GF, J Chem Soc 1958: 1050

    Google Scholar 

  25. Riichardt C and Trautwein H (1962) Chem Ber 95: 1197

    Article  Google Scholar 

  26. Anteunis M and van Schonte J (1963) Bull Soc Chim Belg 72: 787

    Article  CAS  Google Scholar 

  27. Prévost Ch, Gaudemar M, Miginiac L, Bardone-Gaudemar F and Andrac M, Bull Soc Chim France 1959: 769

    Google Scholar 

  28. Walborsky HM and Young AE (1964) J Amer Chem Soc 86: 3288

    Article  CAS  Google Scholar 

  29. Schwartz AM and Johnson JR (1931) J Amer Chem Soc 53: 1063

    Article  CAS  Google Scholar 

  30. Porter CW (1935) J Amer Chem Soc 57: 1436

    Article  CAS  Google Scholar 

  31. Tarbell DS and Weiss M (1939) J Amer Chem Soc 61: 1203

    Article  CAS  Google Scholar 

  32. Walborsky HM and Young AE (1961) J Amer Chem Soc 83: 2595 (1961)

    Google Scholar 

  33. Walborsky HM, Impastato FJ and Young AE (1964) J Amer Chem Soc 86: 3283 and references cited therein.

    Google Scholar 

  34. Walborsky HM, Chen C-J and Webb JL, Tetrahedron Lett 1964: 3551

    Google Scholar 

  35. Walborsky HM and Chen C-J (1971) J Amer Chem Soc 93: 671

    Article  CAS  Google Scholar 

  36. Walborsky HM and Aronoff MS (1973) J Organometal Chem 51: 31

    Article  CAS  Google Scholar 

  37. Walborsky HM and Banks RB (1980) Bull Soc Chim Belg 89: 849

    Article  CAS  Google Scholar 

  38. Walborsky HM and Aronoff MJ (1965) J Organometal Chem 4: 418

    Article  CAS  Google Scholar 

  39. Bodewitz HWHJ, Blomberg C and Bickelhaupt F, Tetrahedron Lett 1972: 281

    Google Scholar 

  40. Closs GL (1969) J Amer Chem Soc 91: 4552

    Article  CAS  Google Scholar 

  41. Kaptein R and Oosterhoff LJ (1969) Chem Phys Lett 4: 214

    Article  CAS  Google Scholar 

  42. Bodewitz HWHJ, Blomberg C and Bickelhaupt F (1973) Tetrahedron 27: 719

    Article  Google Scholar 

  43. Bodewitz HWHJ, Blomberg C and Bickelhaupt F (1975) Tetrahedron 31: 1053

    Article  CAS  Google Scholar 

  44. Bodewitz HWHJ, Blomberg C and Bickelhaupt F, Tetrahedron Lett 1975: 2003

    Google Scholar 

  45. Schaart BJ, Bodewitz HWHJ, Blomberg C and Bickelhaupt F (1976) J Amer Chem Soc 98: 3712

    Article  CAS  Google Scholar 

  46. Bodewitz HWHJ, Schaart BJ, van der Niet JD, Blomberg C, Bickelhaupt F and den Hollander JA (1978) Tetrahedron 34: 2523

    Article  CAS  Google Scholar 

  47. Schaart BJ, Blomberg C, Akkerman OS and Bickelhaupt F (1980) Canad J Chem 58: 932

    Article  CAS  Google Scholar 

  48. Dubois JE, Bauer P, Molle G and Daza J (1977) Compt Rend Sér C 284: 145

    CAS  Google Scholar 

  49. Dubois JE, Molle G, Tourillon G and Bauer P (1979) Tetrahedron Lett 20: 5069

    Article  Google Scholar 

  50. Molle G, Bauer P and Dubois JE (1982) J Org Chem 47: 4120

    Article  CAS  Google Scholar 

  51. Molle G, Dubois JE and Bauer P (1978) Synth Comm 8: 39

    Article  CAS  Google Scholar 

  52. Molle G, Dubois JE and Bauer P (1978) Tetrahedron Lett 19: 3177

    Article  Google Scholar 

  53. Bauer P and Molle G (1978) Tetrahedron Lett. 19: 4853

    Article  Google Scholar 

  54. Molle G and Bauer P (1982) J Amer Chem Soc 104: 3481

    Article  CAS  Google Scholar 

  55. Molle G, Bauer P and Dubois JE (1983) J Org Chem 48: 2975

    Article  CAS  Google Scholar 

  56. Dubois JE, Bauer P and Kaddani B (1985) Tetrahedron Lett 26: 57

    Article  CAS  Google Scholar 

  57. Dubois JE, Bauer P and Briand S (1988) Tetrahedron Lett 29: 3935

    Article  CAS  Google Scholar 

  58. Rogers HR, Hill CL, Fujiwara Y, Rogers RJ, Mitchell HL and Whitesides GM (1980) J Amer Chem Soc 102: 217

    Article  CAS  Google Scholar 

  59. Rogers HR, Deutch J and Whitesides GM (1980) J Amer Chem Soc 102: 226

    Article  CAS  Google Scholar 

  60. Rogers HR, Rogers RJ, Mitchell HL and Whitesides GM (1980) J Amer Chem Soc 102: 231

    Article  CAS  Google Scholar 

  61. Barber JJ and Whitesides GM (1980) J Amer Chem Soc 102: 239

    Article  CAS  Google Scholar 

  62. Root KS, Deutch J and Whitesides GM (1981) J Amer Chem Soc 103: 5475

    Article  CAS  Google Scholar 

  63. Lawrence LM and Whitesides GM (1980) J Amer Chem Soc 102: 2493

    Article  CAS  Google Scholar 

  64. Garst JF, Deutch JE and Whitesides GM (1986) J Amer Chem Soc 108: 2490

    Article  CAS  Google Scholar 

  65. Ashby EC and Oswald J (1988) J Org Chem 53: 6068

    Article  CAS  Google Scholar 

  66. Walborsky HM and Zimmermann C (1992) J Amer Chem Soc 114: 4996

    Article  CAS  Google Scholar 

  67. Garst JF, Ungvary F, Batlaw R and Lawrence EL (1991) J Amer Chem Soc 113: 5392

    Article  CAS  Google Scholar 

  68. Walborsky HM and Rachon J (1989) J Amer Chem Soc 111: 1896

    Article  CAS  Google Scholar 

  69. Rachin J and Walborsky HM (1989) Tetrahedron Lett 30: 7345

    Article  Google Scholar 

  70. Walborsky HM (1990) Acc Chem Res 23: 286

    Article  CAS  Google Scholar 

  71. Crandall JK and Magaha HS (1982) J Org Chem 47: 5368

    Article  CAS  Google Scholar 

  72. Cameron GG and Milton AJS, J Chem Soc Perkin Trans. II, 1976: 378

    Google Scholar 

  73. Killinger TA, Boughton NA, Runge TA and Wolinsky J (1977) J Organometal Chem 124: 131

    Article  CAS  Google Scholar 

  74. Pearce PJ, Richards DH and Scilly NF, J Chem Soc D 1970: 1160

    Google Scholar 

  75. Pearce PJ, Richards DH and Scilly NF, J Chem Soc Perkin Trans I 1972: 1655

    Google Scholar 

  76. Pearce PJ, Richards DH and Scilly NF (1974) British Patent 1335, 1975, 140. Chem Abstr 80: 70306

    Google Scholar 

  77. Garst JF and Smith CD (1976) J Amer Chem Soc 98: 1520

    Article  CAS  Google Scholar 

  78. Bryce-Smith D and Wakefield BJ, Tetrahedron Lett 1964: 3295

    Google Scholar 

  79. Blomberg C and Mosher HS (1968) J Organometall Chem 13: 519

    Article  CAS  Google Scholar 

  80. Ashby EC, Buhler JD, Lopp IG, Wieseman TL, Bowers Jr JC and Laemrnle JT (1976) J Amer Chem Soc 98: 6561

    Article  CAS  Google Scholar 

  81. Okubo M (1977) Bull Chem Soc Japan 50: 2379

    Article  CAS  Google Scholar 

  82. Hartog FA (1978) Thesis Free University Amsterdam Available on request.

    Google Scholar 

  83. Ashby EC and Goel AB (1977) J Amer Chem Soc 99: 310

    Article  CAS  Google Scholar 

  84. Givelet MHE (1968) Compt Rend Sér C 278: 881

    Google Scholar 

  85. Givelet MHE (1969) French Patent 1541058, (1968); Chem Abstr 70: 25265y

    Google Scholar 

  86. Fuson RC, Armstrong MD and Speck SB (1942) J Org Chem 7: 297

    Article  CAS  Google Scholar 

  87. Holm T and Crossland I (1971) Acta Chem Scand 25: 56

    Google Scholar 

  88. Ashby EC, Laemmle JT and Neumann HM (1974) Acc Chem Res 7: 272

    Article  CAS  Google Scholar 

  89. Ashby EC and Laemmle JT (1975) Chem Rev 75: 521

    Article  CAS  Google Scholar 

  90. Katzenellengbogen JA and Lenox RS (1973) J Org Chem 38: 326

    Article  Google Scholar 

  91. Blancou H, Morreau P and Commeyras A, J Chem Soc Chem Comm 1976: 885

    Google Scholar 

  92. Boldrini GP, Savoia D, Tagliavini A, Trombini C and Umani-Ronchi A (1983) J Org Chem 48: 4108

    Article  CAS  Google Scholar 

  93. Uneyama K, Matsuda H and Torii S (1984) Tetrahedron Lett 25: 6017

    Article  CAS  Google Scholar 

  94. de Souza-Barbosa JC, Luche J-L and Pétrier C (1987) Tetrahedron Lett 28: 2013

    Article  Google Scholar 

  95. de Souza-Barboza JC, Pétrier C and Luche J-L (1988) J Org Chem 53: 1212

    Article  CAS  Google Scholar 

  96. Moyano A, Pericàs MA, Riera A and Luche J-L (1990) Tetrahedron Lett 31: 7619

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1993 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Blomberg, C. (1993). The Mechanism of the Barbier Reaction. In: The Barbier Reaction and Related One-Step Processes. Reactivity and Structure: Concepts in Organic Chemistry, vol 31. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-85019-6_4

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-85019-6_4

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-85021-9

  • Online ISBN: 978-3-642-85019-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics