Skip to main content
SpringerLink
Log in

[2,3]Sigmatropic Rearrangements of Propargylic and Allenic Systems

  • Chapter
  • First Online:
Sulfur-Mediated Rearrangements II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 275))

Abstract

[2,3]Sigmatropic rearrangements of propargyl sulfonium ylides along with recent advances in the correspondingsulfenate–sulfoxide and sulfinate–sulfone type rearrangements are reviewed. Some new additionalexamples of these types of transformations, including rearrangements of propargylic dialkoxy disulfidesare also surveyed.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover 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.

Abbreviations

S-TBSP:

1-[(4-t-Butylphenyl)sulfonyl]-(2S)-pyrrolidinecarboxylate)

S-DOSP:

1-[(4-Alkyl(C11-C13)phenyl)sulfonyl]-(2S)-pyrrolidinecarboxylate)

NB:

2-Nitrophenyl

BMCB:

Bis(methylene)cyclobutene

dpph:

Bis(diphenylphosphino)hexane

dppb:

Bis(diphenylphosphino)butane

References

  1. Braverman S (1963) PhD thesis, University of Alberta

    Google Scholar 

  2. Darwish D, Braverman S (1965) 48th Chem institute of Canada conference, Montreal, Canada, 1965

    Google Scholar 

  3. Braverman S (1971) Int J Sulfur Chem C 6:149

    CAS  Google Scholar 

  4. Braverman S, Stabinsky Y (1967) Chem Commun (London) 270

    Google Scholar 

  5. Miller EG, Rayner DR, Mislow K (1966) J Am Chem Soc 88:3139

    Article  CAS  Google Scholar 

  6. Braverman S, Mechoulam H (1974) Tetrahedron 30:3883

    Article  CAS  Google Scholar 

  7. Braverman S, Mechoulam H (1967) Isr J Chem 5:71

    CAS  Google Scholar 

  8. Braverman S, Stabinsky Y (1967) Isr J Chem 5:125

    CAS  Google Scholar 

  9. Braverman S (1988) In: Patai S, Rappoport Z, Stirling C (eds) The chemistry of sulphones and sulphoxides. Wiley, New York, p 717

    Chapter  Google Scholar 

  10. Braverman S (1988) In: Patai S, Rappoport Z, Stirling C (eds) The chemistry of sulphones and sulphoxides. Wiley, New York, p 665

    Chapter  Google Scholar 

  11. Braverman S (1990) In: Patai S (ed) The chemistry of sulphinic acids, esters and their derivatives. Wiley, New York, p 297

    Chapter  Google Scholar 

  12. Braverman S (1990) In: Patai S (ed) The chemistry of sulphenic acids and their derivatives. Wiley, New York, p 311

    Chapter  Google Scholar 

  13. Baldwin JE, Hackler RE, Kelly DP (1968) Chem Commun (London) 1083

    Google Scholar 

  14. Baldwin JE, Hackler RE, Kelly DP (1968) Chem Commun (London) 538

    Google Scholar 

  15. Grieco PA, Meyers M, Finkelhor RS (1974) J Org Chem 39:119

    Article  CAS  Google Scholar 

  16. Pourcelot G, Veniard L, Cadiot P (1975) Bull Soc Chim Fr 1275

    Google Scholar 

  17. Pourcelot G, Veniard L, Cadiot P (1975) Bull Soc Chim Fr 1281

    Google Scholar 

  18. Hill RK (1984) In: Morrison JD (ed) Asymmetric synthesis: stereodifferentiating addition reactions, part B, vol 3. Academic, New York, p 503

    Google Scholar 

  19. Stevenart-De Mesmaeker N, Merenyi R, Viehe HG (1987) Tetrahedron Lett 28:2591

    Article  CAS  Google Scholar 

  20. Braverman S, Zafrani Y, Rahimipour S (2001) Tetrahedron Lett 42:2911

    Article  CAS  Google Scholar 

  21. Braverman S, Zafrani Y, Gottlieb HE (2001) Tetrahedron 57:9177

    Article  CAS  Google Scholar 

  22. Cagle PC, Arif AM, Gladysz JA (1994) J Am Chem Soc 116:3655

    Article  CAS  Google Scholar 

  23. Cagle PC, Meyer O, Weickhardt K, Arif AM, Gladysz JA (1995) J Am Chem Soc 117:11730

    Article  CAS  Google Scholar 

  24. Meyer O, Cagle PC, Weickhardt K, Vichard D, Gladysz JA (1996) Pure Appl Chem 68:79

    Article  CAS  Google Scholar 

  25. Kirmse W, Kapps M (1968) Chem Ber 101:994

    Article  CAS  Google Scholar 

  26. Doyle MP, Griffin JH, Chinn MS, Van Leusen D (1984) J Org Chem 49:1917

    Article  CAS  Google Scholar 

  27. Doyle MP (1986) Acc Chem Res 19:348

    Article  CAS  Google Scholar 

  28. Hodgson DM, Pierard FYTM, Stupple PA (2001) Chem Soc Rev 30:50

    Article  CAS  Google Scholar 

  29. Padwa A, Hornbuckle SF (1991) Chem Rev 91:263

    Article  CAS  Google Scholar 

  30. Shi G, Xu Y, Xu M (1991) Tetrahedron 47:1629

    Article  CAS  Google Scholar 

  31. Prabharasuth R, Van Vranken DL (2001) J Org Chem 66:5256

    Article  CAS  Google Scholar 

  32. Kido F, Abiko T, Kato M (1992) Bull Chem Soc Jpn 65:2471

    Article  CAS  Google Scholar 

  33. Nishibayashi Y, Ohe K, Uemura S (1995) J Chem Soc Chem Commun 1245

    Google Scholar 

  34. Zhang X, Ma M, Wang J (2003) Tetrahedron: Asymmetry 14:891

    Article  CAS  Google Scholar 

  35. Zhang X-M, Ma M, Wang J-B (2003) Chinese J Chem 21:878

    Article  CAS  Google Scholar 

  36. Ma M, Peng L, Li C, Zhang X, Wang J (2005) J Am Chem Soc 127:15016

    Article  CAS  Google Scholar 

  37. Tamura Y, Ikeda H, Mukai C, Morita I, Ikeda M (1981) J Org Chem 46:1732

    Article  CAS  Google Scholar 

  38. Armstrong A, Cooke RS (2002) Chem Commun 904

    Google Scholar 

  39. Armstrong A, Cooke RS, Shanahan SE (2003) Org Biomol Chem 1:3142

    Article  CAS  Google Scholar 

  40. Bach T, Koerber C (2000) J Org Chem 65:2358

    Article  CAS  Google Scholar 

  41. Bach T, Koerber C (1999) Eur J Org Chem 1033

    Google Scholar 

  42. Bach T, Koerber C (1998) Tetrahedron Lett 39:5015

    Article  CAS  Google Scholar 

  43. Bacci JP, Greenman KL, Van Vranken DL (2003) J Org Chem 68:4955

    Article  CAS  Google Scholar 

  44. Smith G, Stirling CJM (1971) J Chem Soc C 1530

    Google Scholar 

  45. Padwa A, Bullock WH, Norman BH, Perumattam J (1991) J Org Chem 56:4252

    Article  CAS  Google Scholar 

  46. Padwa A, Norman BH, Perumattam J (1989) Tetrahedron Lett 30:663

    Article  CAS  Google Scholar 

  47. Braverman S, Lior Z (1994) Tetrahedron Lett 35:6725

    Article  CAS  Google Scholar 

  48. Iglesias B, Torrado A, De Lera AR, Lopez S (2000) J Org Chem 65:2696

    Article  CAS  Google Scholar 

  49. Conrads M, Mattay J (1991) Synthesis 11

    Google Scholar 

  50. Christov VC, Prodanov B, Nikolova R (2000) Phosphorus Sulfur Silicon Relat Elem 166:275

    Article  CAS  Google Scholar 

  51. Saalfrank RW, Welch A, Haubner M, Bauer U (1996) Liebigs Ann Chem 171

    Google Scholar 

  52. Christov VC, Ivanov IK (2002) Phosphorus Sulfur Silicon Relat Elem 177:2445

    Article  CAS  Google Scholar 

  53. Christov VC, Ivanov IK (2002) Sulfur Lett 25:191

    Article  CAS  Google Scholar 

  54. Braverman S, Kumar EVKS, Cherkinsky M, Sprecher M, Goldberg I (2005) Tetrahedron 61:3547

    Article  CAS  Google Scholar 

  55. Huntsman WD, Wristers HJ (1967) J Am Chem Soc 89:342

    Article  CAS  Google Scholar 

  56. Kleveland K, Skattebol L (1973) J Chem Soc Chem Commun 432

    Google Scholar 

  57. Pasto DJ, Yang SH (1989) J Org Chem 54:3544

    Article  CAS  Google Scholar 

  58. Toda F, Tanaka K, Tamashima T, Kato M (1998) Angew Chem Int Ed Engl 37:2724

    Article  CAS  Google Scholar 

  59. Birsa ML, Jones PG, Braverman S, Hopf H (2005) Synlett 640

    Google Scholar 

  60. Baudin JB, Julia SA, Lorne R (1992) Bull Soc Chim Fr 129:440

    CAS  Google Scholar 

  61. Baudin JB, Julia SA, Lorne R (1991) Synlett 509

    Google Scholar 

  62. Majumdar KS, Thyagarajan BS (1972) J Chem Soc Chem Commun 83

    Google Scholar 

  63. Aoyagi S, Makabe M, Shimada K, Takikawa Y (2000) 19th International Symposium organic chemistry of sulfur (ISOCS 19), Sheffield, UK, p 50

    Google Scholar 

  64. Posner GH, Carry JC, Crouch RD, Johnson N (1991) J Org Chem 56:6987

    Article  CAS  Google Scholar 

  65. Wang X, Ni Z, Lu X, Hollis A, Banks H, Rodriguez A, Padwa A (1993) J Org Chem 58:5377

    Article  CAS  Google Scholar 

  66. Braverman S, Mechoulam H (1966) Isr J Chem 4:17

    Google Scholar 

  67. Stirling CJM (1967) Chem Commun (London) 131

    Google Scholar 

  68. Hiroi K, Kato F (2001) Tetrahedron 57:1543

    Article  CAS  Google Scholar 

  69. Hiroi K, Kato F, Nakasato H (1998) Chem Lett 553

    Google Scholar 

  70. Braverman S, Grinstein D, Lior Z (1993) Phosphorus Sulfur Silicon Relat Elem 74:443

    Article  CAS  Google Scholar 

  71. Braverman S, Pechenick T, Zafrani Y (2004) ARKIVOC 51

    Google Scholar 

  72. Braverman S, Pechenick T, Zafrani Y (2001) Tetrahedron Lett 42:1391

    Article  CAS  Google Scholar 

  73. Klunder JM, Sharpless KB (1987) J Org Chem 52:2598

    Article  CAS  Google Scholar 

  74. Braverman S, Manor H (1990) Phosphorus Sulfur Silicon Relat Elem 53:357

    Article  CAS  Google Scholar 

  75. Braverman S, Duar Y (1990) Tetrahedron 46:2975

    Article  CAS  Google Scholar 

  76. Harzdorf C, Meussdoerffer J-N, Niederprum H, Wechsberg M (1973) Justus Liebigs Ann Chem 33

    Google Scholar 

  77. van der Linden JB, van Asten PFTM, Braverman S, Zwanenburg B (1995) Rec Trav Chim Pays-Bas 114:51

    Article  Google Scholar 

  78. Christov V, Ivanov I (2004) Phosphorus Sulfur Silicon Relat Elem 179:1681

    Article  CAS  Google Scholar 

  79. Christov VC, Ivanov IK (2003) Heterocycl Commun 9:629

    Article  CAS  Google Scholar 

  80. Saalfrank RW, Bauer U, Hilbig K, Welch A (1993) Chem Ber 126:823

    Article  CAS  Google Scholar 

  81. Baudin J-B, Julia SA, Wang Y (1995) Bull Soc Chim Fr 132:739

    CAS  Google Scholar 

  82. Baudin JB, Bkouche-Waksman I, Julia SA, Pascard C, Wang Y (1991) Tetrahedron 47:3353

    Article  CAS  Google Scholar 

  83. Block E (1992) Angew Chem Int Ed Engl 31:1135

    Article  Google Scholar 

  84. Braverman S, Pechenick T, Gottlieb HE (2003) Tetrahedron Lett 44:777

    Article  CAS  Google Scholar 

  85. Braverman S, Pechenick T, Gottlieb HE, Sprecher M (2003) J Am Chem Soc 125:14290

    Article  CAS  Google Scholar 

  86. Freeman F (1984) Chem Rev 84:117

    Article  CAS  Google Scholar 

  87. Lacombe SM (1999) Rev Heteroatom Chem 21:1

    CAS  Google Scholar 

  88. Braverman S, Pechenick T, Gottlieb HE, Sprecher M (2004) Tetrahedron Lett 45:8235

    Article  CAS  Google Scholar 

  89. Braverman S, Segev D (1974) J Am Chem Soc 96:1245

    Article  CAS  Google Scholar 

  90. Braverman S, Zafrani Y, Gottlieb HE (2001) Tetrahedron 57:9177

    Article  CAS  Google Scholar 

  91. Braverman S, Pechenick T (2003) Synthesis 2079

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Bar-Ilan University, 52900, Ramat-Gan, Israel

    Samuel Braverman & Marina Cherkinsky

Authors
  1. Samuel Braverman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marina Cherkinsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Samuel Braverman .

Editor information

Ernst Schaumann

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Braverman, S., Cherkinsky, M. (2006). [2,3]Sigmatropic Rearrangements of Propargylic and Allenic Systems. In: Schaumann, E. (eds) Sulfur-Mediated Rearrangements II. Topics in Current Chemistry, vol 275. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_047

Download citation

Publish with us

Policies and ethics

Search

Navigation