Advertisement

Novel organic peroxygen reagents for use in organic synthesis

  • Harry Heaney
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 164)

Abstract

In this review, I will discuss recent work involving new safe peroxidic reagents that have been developed in order to overcome some of the hazards associated with reagents that have been used in the past but which are now no longer in favour. I will also comment on other work using the reagents that my coworkers and I have developed and also, where appropriate, draw comparisons with other peroxygen reagents, especially m-chloroperoxy-benzoic acid (MCPBA).

Keywords

Styrene Oxide Epoxidation Reaction Alkaline Hydrogen Peroxide Disodium Hydrogen Phosphate Trifluoroacetic Anhydride 
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.

6 References

  1. 1.
    UN test method, Test 2 (b) (iii)-ST/AG/AC 10/11Google Scholar
  2. 2.
    Schwartz NN, Blumbergs JH (1964) J Org Chem, 29: 1976Google Scholar
  3. 3.
    European Patent Appl 27693 (1981); Chem Abs (1981) 95: 168801Google Scholar
  4. 4.
    Available from Interox Chemicals Ltd, Baronet Works, P.O. Box 7, Warrington, Cheshire, WA46HB, U.K. Also from Aldrich Chemical Company LtdGoogle Scholar
  5. 5.
    Brougham P, Cooper MS, Cummerson DA, Heaney H, Thompson N (1987) Synthesis 1015Google Scholar
  6. 6.
    Cookson PG, Davies AG, Fazal N (1975) J Organometal Chem, 99: C31Google Scholar
  7. 7.
    Oswald AA, Guertin DL (1963) J Org Chem, 28: 651–657Google Scholar
  8. 8.
    Temple RD, Tsuno Y, Leffler JE (1963) J Org Chem 28: 2495; Copley DB, Fairbrother F, Miller JR, Thompson A (1964) Proc Chem Soc, 300–301Google Scholar
  9. 9.
    Lu C-S, Hughes EW, Giguère PA (1941) J Am Chem Soc, 63: 1507–1513Google Scholar
  10. 10.
    Aida K (1963) J Inorg Nucl Chem, 25: 165–170Google Scholar
  11. 11.
    Cooper MS, Heaney H, Newbold AJ, Sanderson WR (1990) 533–535Google Scholar
  12. 12.
    Jackson WP (1990) Synlett 536Google Scholar
  13. 13.
    Fieser LF, Fieser M (1967) Reagents for organic synthesis, vol 1, J Wiley, New York, pp 135–139Google Scholar
  14. 14.
    Borowitz IJ, Gonis G (1964) Tetrahedron Lett, 1151–1155Google Scholar
  15. 15.
    Delia TJ, Olsen MJ, Brown GB (1965) J Org Chem, 30: 2766–2768Google Scholar
  16. 16.
    Gillard JR, Newlands MJ, Bridson JN, Burnell DJ (1991) Canad J Chem, 69: 1337–1343Google Scholar
  17. 17.
    Paquette LA, Barrett JH (1973) Org Synth, Coll Vol V, 467–471Google Scholar
  18. 18.
    Semmelhack MF, Zask A (1983) J Am Chem Soc, 105: 2034–2043Google Scholar
  19. 19.
    Machida S, Hashimoto Y, Saigo K, Inoue J-y, Hasegawa (1991) 47: 3737–3752Google Scholar
  20. 20.
    Grandjean D, Pale P, Chuche (1991) Tetrahedron Lett, 32: 3043–3046Google Scholar
  21. 21.
    Kishi Y, Aratani M, Tanino H, Fukuyama T, Goto T, Inoue S, Sugiura S, Kakoi H (1972) J Chem Soc, Chem Commun, 64–65Google Scholar
  22. 22.
    Petter RC (1989) Tetrahedron Lett, 30: 399–402Google Scholar
  23. 23.
    Querci C, Ricci M (1989) J Chem Soc, Chem Commun, 889–890Google Scholar
  24. 24.
    Yamada T, Takai T, Rhode O, Mukaiyama T (1991) Bull Chem Soc Jpn, 64: 2109–2117Google Scholar
  25. 25.
    Marples BA, Muxworthy JP, Baggaley KH, (1991) Tetrahedron Lett, 32: 533–536Google Scholar
  26. 26.
    Kang SH, Kim WJ (1989) Tetrahedron Lett, 30: 5915–5918Google Scholar
  27. 27.
    Chang HM, Chui KY, Tan FWL, Yang Y, Zhong ZP (1991) J Med Chem, 34: 1675–1692Google Scholar
  28. 28.
    Newman H, Angier RB (1970) Tetrahedron, 26: 825–836Google Scholar
  29. 29.
    Sharpless KB, Michaelson RC, (1973) J Am Chem Soc, 95: 6136–6137Google Scholar
  30. 30.
    Nakamura M, Tsutsuki N, Takeda T, Rokroyama T, (1984) Tetrahedron Lett, 25: 3231–3232Google Scholar
  31. 31.
    Jefford CW, Jaggi D, Boukouvalas J (1989) Tetrahedron Lett, 30: 1237–1240Google Scholar
  32. 32.
    Dominguez C, Csáky AG, Plumet J (1990) Tetrahedron Lett, 31: 7669–7670.Google Scholar
  33. 33.
    Conway SC, Gribble GW (1990), Heterocycles 30: 627–633Google Scholar
  34. 34.
    Kocovsky P (1988) Tetrahedron Lett, 29: 2475–2478Google Scholar
  35. 35.
    Harmat NJS, Warren S (1990) Tetrahedron Lett, 31: 2743–2746Google Scholar
  36. 36.
    Houk KN, Moses SR, Wu Y-D, Rondan NG, Jäger V, Schohe R, Fronczek FR (1984) J Am Chem. Soc, 106: 3880–3882Google Scholar
  37. 37.
    Fleming I, Sarkar AK, Thomas AP (1987) J Chem Soc, Chem Commun, 157–159Google Scholar
  38. 38.
    Stork G, Kahn M (1983) Tetrahedron Lett, 24: 3951–3954Google Scholar
  39. 39.
    Lewis SN (1969) In: Augustine RL Oxidation (ed) vol 1, Dekker, New York, pp 213–258Google Scholar
  40. 40.
    Anastasia M, Allevi P, Ciuffreda P, Fiecchi A, Scala A (1985) J Org Chem, 50: 321–325Google Scholar
  41. 41.
    Noyori R, Sato T, Hayakawa Y (1978) J Am Chem Soc, 100: 2561–2563Google Scholar
  42. 42.
    Suginome J, Yamada S (1986) Synthesis, 741–743Google Scholar
  43. 43.
    Ricci M, Altamura M, Bianchi D, Cobri W, Gotti N (1988) to Farmitalia Carlo Erba, Spa, GB Pat 2196340Google Scholar
  44. 44.
    Professor Eaton PE, (February 1991) University of Chicago, Personal CommunicationGoogle Scholar
  45. 45.
    Godfrey IM, Sargent MV, Elix JA (1974) J Chem Soc, Perkin Trans 1, 1353–1354Google Scholar
  46. 46.
    van den Broek LAGM, in't Veld PJA, Colstee JH, Ottenheijm HCJ (1989) Synth Commun, 19: 3397–3405Google Scholar
  47. 47.
    Batty D, Crich D, Fortt SM (1990) J Chem Soc, Perkin Trans. 1 2875–2879Google Scholar
  48. 48.
    Crich D, Ritchie TJ (1990) J Chem Soc, Perkin Trans. 1 945–954Google Scholar
  49. 49.
    Siemens LM, Rottnek FW, Trzupek LS (1990) J Org Chem, 55, 3507–3511Google Scholar
  50. 50.
    Lamsa J, to Oy Farmos-Yhtymä (1987) Euro Pat 0270201Google Scholar
  51. 51.
    Klemm LH, Wang J, Sur SK (1990) J Heterocycl Chem, 27: 1537–1541Google Scholar
  52. 52.
    Eichler E, Rooney CS, Williams HWR (1976) J Heterocycl Chem, 13: 41–42Google Scholar
  53. 53.
    Holmes AB, Hughes AB, Smith AL (1991) Synlett 47–48Google Scholar
  54. 54.
    Enders D (1984) In: Morrison JD (ed) Asymmetric synthesis, vol 3 Academic, Orlando, pp 275–339Google Scholar
  55. 55.
    McKilop A, Tarbin JA (1987) Tetrahedron, 43: 1753–1758Google Scholar
  56. 56.
    Enders D, Plant A (1990) Synlett 725–726Google Scholar
  57. 57.
    Wagner J, Vogel P (1991) Tetrahedron, 47: 9641–9658Google Scholar
  58. 58.
    Forbes JE, Bowden MC, Pattenden G (1991) J chem Soc, Perkin Trans, 1: 1967–1973Google Scholar
  59. 59.
    Avery MA, Chong WKM, Jennings-White C (1992) J Am Chem Soc, 114: 949–979Google Scholar
  60. 60.
    Gonsalves AMR, Johnstone RAW, Pereira MM, Shaw J (1991) J Chem Res S, 208–209Google Scholar
  61. 61.
    Back TG, Blazecka PG, Krishna MV (1991) Tetrahedron Lett, 4817–4818Google Scholar
  62. 62.
    Barton DHR, Bévière SD, Chavasiri W, Csuhai E, Doller D, Liu W-G (1992) J Am Chem Soc, 114: 2147–2156Google Scholar

Copyright information

© Springer-Verlag 1993

Authors and Affiliations

  • Harry Heaney
    • 1
  1. 1.Department of ChemistryLoughborough University of TechnologyUK

Personalised recommendations