The anionic phospho-fries rearrangement

Current Organic Chemistry

Volumn 8, Issue 7, 2004, Pages 623-636

  Taylor, C M ^a   Watson, A J ^a  

^a MASSEY UNIVERSITY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

'CURRENT; ARYL PHOSPHATE; FRIES REARRANGEMENT; HYDROGEN EXCHANGE; METAL-HYDROGEN; METALLATION; OH -; ORTHO POSITION; PHOSPHATE ESTERS; PHOSPHATE GROUP;

IONS;

ANION; AROMATIC COMPOUND; CARBON; NAPHTHOL DERIVATIVE; ORGANOPHOSPHATE; ORGANOPHOSPHORUS COMPOUND; PHENOL DERIVATIVE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHORUS; PODOCARPIC ACID DERIVATIVE;

ASYMMETRIC CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; METALLATION; PHOSPHORYLATION; RELIABILITY; REVIEW; ROOM TEMPERATURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 1942534669     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043370717     Document Type: Review

References (60)

1. Fries, K.; Finck, G. Ber. 1909, 41, 4271-4284.
2. Blatt, A. H. Chem. Rev. 1940, 27, 413-436.
3. Blatt, A. H. Org. React. 1942, 342-369.
4. Martin, R. Org. Prep. Proc. Intl 1992, 24, 369-435.
5. Hellwinkel, D.; Lammerzahl, F.; Hofmann, G. Chem. Ber. 1983, 3375-3405.
6. Miller, J. A. J. Org. Chem. 1987, 52, 322-323.
7. Shafer, S. J.; Closson, W. D. J. Org. Chem. 1975, 40, 889-892.
8. Häbich, D.; Effenberger, F. Synthesis 1979, 841-876.
9. Sibi, M. P.; Snieckus, V. J. Org. Chem. 1983, 48, 1935-1937.
10. Hallberg, A.; Svensson, A.; Martin, A. R. Tetrahedron Lett. 1986, 27, 1959-1962.
11. Eymery, F.; Iorga, B.; Savignac, P. Tetrahedron 1999, 55, 13109-13150.
12. Cushman, M.; Wang, P.; Chang, S. H.; Wild, C.; De Clercq, E.; Schols, D.; Goldman, M. E. Bowen, J. A. J. Med. Chem. 1991, 34, 329-337.
13. For example, the utilization of phosphonates as transition-state analogues for peptide bond hydrolysis: Bartlett P. A.; Marlowe, C. K.; Giannousis, P. P.; Hanson, J. E. Cold Spring Harbor Symp. Quant. Biol. 1987, 52, 83-90.
14. Brunel, J. M.; Constantieux, T.; Legrand, L.; Buono, G. Tetrahedron Lett. 1998, 39, 2961-2964.
15. Legrand, O.; Brunel, J. M.; Buono, G. Tetrahedron Lett. 2000, 41, 2105-2109.
16. Yang, Z. H.; Zhou, Z. H.; Wang, L. X.; Li, K. Y.; Zhou, Q. L.; Tang, C. C. Synth. Commun. 2002, 32, 2751-2756.
17. Brunel, J. M.; Legrand, O.; Buono, G. Eur. J. Org. Chem. 2000, 3313-3321.
18. Wang, C. S.; Shieh, J. Y. J. Appl. Polymer Sci. 1999, 73, 353-361.
19. Wang, C. S.; Lin, C. S. J. Appl. Polymer Sci. 2000, 75, 429-436.
20. Wang, C. S.; Lee, M. C. Polymer 2000, 41, 3631-3638.
21. Shieh, J. Y.; Wang, C. S. J. Polymer Sci. A 2001, 40, 369-378.
22. Liu, Y. L.; Chia, Y. C.; Wu, C. S. J. Appl. Polymer Sci. 2002, 87, 404-411.
23. Sun, Y. M.; Wang, C. S. Polymer 2001, 42, 1035-1045.
24. Sun, Y. M.; Hung, A. Y. C.; Wang, C. T. J. Appl. Polymer Sci. 2002, 85, 2367-2376.
25. Alberts, A. H.; Timmer, K.; Noltes, J. G.; Spek, A. L. J. Am. Chem. Soc. 1979, 101, 3375-3376.
26. Wehner, M.; Schrader, T.; Finocchiaro, P.; Failla, S.; Consiglio, G. Org. Lett. 2000, 2, 605-608.
27. Consiglio, G. A.; Finocchiaro, P.; Failla, S.; Hardcastle, K. I.; Ross, C.; Caccamese, S.; Giudice, G. Eur. J. Org. Chem. 1999, 2799-2806.
28. Melvin, L. S. Tetrahedron Lett. 1981, 22, 3375-3376.
29. Melvin. L. S.; Bordner, J.; Hada, W. A.; Johnson, M. R. J. Heterocyclic Chem. 1990, 27, 535-547.
30. Cambie, R. C.; Palmer, B. D. Aust. J. Chem. 1982, 35, 827-837.
31. Kenner, G. W.; Williams, N. R. J. Chem. Soc., Abstracts 1955, 522-525.
32. Dhawan, B.; Redmore, D. J. Org. Chem. 1984, 49, 4018-4021.
33. Dhawan, B.; Redmore, D. Synth. Commun. 1985, 15, 411-416.
34. Dhawan, B.; Redmore, D. Phosphorus Sulfur and Silicon 1989, 42, 177-182.
35. Dhawan, B.; Redmore, D. Phosphorus, Sulfur and Silicon 1991, 61, 183-187.
36. Gajda,T.; Zwerzak, A. Synthesis 1976, 243.
37. Casteel, D. A.; Peri, S. P. Synthesis 1991, 691-693.
38. Li, S.; Wang, G. Phosphorus. Sulfur and Silicon 1991, 61, 119-129.
39. Heinicke, J.; Böhle, I.; Tzschach, A. J. Organomet. Chem. 1986, 317, 11-21.
40. Dhawan, B.; Redmore, D. J. Chem. Res. (S) 1988, 222-223.
41. Näsman, J. H.; Kopola, N.; Pensar, G. Tetrahedron Lett. 1986, 27, 1391-1394.
42. Näsman, J. H.; Kopola, N. Synth. Commun. 1992, 22, 2491-2498.
43. Watanabe, M.; Date, M.; Kawanishi, K.; Hori, T.; Furukawa, S. Chem. Pharm. Bull. 1990, 38, 2637-2643.
44. Legrand, O.; Brunel, J. M.; Constantieux, T.; Buono, G. Chem. Eur. J. 1998, 4, 1061-1067.
45. Legrand, O.; Brunel, J. M.; Buono, G. Eur. J. Org. Chem. 1999, 1099-1105.
46. Welch, S. C.; Levine, J. A.; Bernal, I.; Cetrullo, J. J. Org. Chem. 1990, 55, 5991-5995.
47. Heinicke, J.; Tzschach, A. Z. Chem. 1983, 23, 439-440.
48. Legrand, O.; Brunel, J. M.; Buono, G. Tetrahedron 2000, 56, 595-603.
49. Coll, G.; Morey, J.; Costa, A.; Saá, J. M. J. Org. Chem. 1988, 53, 5345-5448.
50. Dhawan, B.; Redmore, D. J. Org. Chem. 1991, 56, 833-835.
51. Au-Yeung, T. L.; Chan, K. Y.; Haynes, R. K.; Williams, I. D.; Yeung, L. L. Tetrahedron Lett. 2001, 42, 457-460.
52. Crowther, G. P.; Sandberg, R. J.; Sarpeshkar, A. M. J. Org. Chem. 1984, 49, 4657.
53. Dhawan, B.; Redmore, D. J. Org. Chem. 1986, 51, 179-183.
54. Heinicke, J.; Kadyrov, R.; Kellner, K.; Nietzschmann, E.; Tzschach, A. Phosphorus. Sulfur, Silicon 1989, 44, 209-216.
55. Dhawan, B.; Redmore, D. Synth. Commun. 1987, 17, 465-468.
56. Paladino, J.; Guyard, C.; Thurieaux, C.; Fauchère, J.-L. Helv. Chim. Acta 1993, 76, 2465-2472.
57. Schöllkopf, U.; Groth, U.; Deng, C. Angew Chem., Int. Ed. Engl. 1981, 20, 798-799.
58. Koszuk, J. F.; Czech, B. P.; Walkowiak, W.; Babb, D. A.; Bartsch, R. A. J.C.S., Chem. Commun. 1984, 1504-1505.
59. Czech, B. P.; Desai, D. H.; Koszuk, J.; Czech, A.; Babb, D. A.; Robison, T. W.; Bartsch, R. A. J. Heterocyclic Chem. 1992, 29, 867-875.
60. Consiglio, G. A.; Failla, S.; Finocchiaro, P.; Hardcastle, K. I. Phosphorus Sulfur Silicon Rel. El. 1999, 144-146, 697-700.