Organic synthesis using a migrating functional group: [1,2] and [1,3] phenylthio shifts in synthesis via allyl sulphides

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 10, 1977, Pages 1131-1141

  Brownbridge, Peter ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011867014     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19770001131     Document Type: Article

References (84)

1. Preliminary communication, P. Brownbridge and S. Warren, J.C.S. Chem. Comm., 1975, 820.
2. E. J. Corey, Pure Appl. Chem., 1967, 14, 19.
3. D. Seebach and M. Kolb, Chem. And Ind., 1974, 687.
4. D.A. Evans and G. C. Andrews, Accounts Chem. Res., 1974, 7, 147.
5. B. M. Trost, K. Hiroi, and S. Kurozumi, J. Amer. Chem. Soc., 1975, 97, 438.
6. B. M. Trost and K. Hiroi, J. Amer. Chem. Soc., 1975, 97, 6911.
7. P. K. G. Hodgson and S. Warren, J.C.S. Perkin II, 1975, 372.
8. T. H. Phan and H. Dahn, Helv. Chim. Acta, 1976, 59, 335.
9. D. Howells and S. Warren, J.C.S. Perkin II, 1973, 1472.
10. A. H. Davidson, P. K. G. Hodgson, D. Howells, and S. Warren, Chem. And Ind., 1975, 455.
11. A. H. Davidson and S. Warren, J.C.S. Chem. Comm., 1975, 148
12. A. H. Davidson and S. Warren J.C.S. Perkin I, 1976, 639.
13. P. K. G. Hodgson, R. G. Shepherd, and S. Warren, J.C.S. Chem. Comm., 1974, 633
14. P. Brownbridge, P. K. G. Hodgson, R. G. Shepherd, and S. Warren, J.C.S. Perkin I, 1976, 2024.
15. B. M. Trost and J. L. Stanton, J.Amer. Chem. Soc., 1975, 97, 4018.
16. H. Gilman and F. J. Webb, J. Amer. Chem. Soc., 1949, 71, 4062
17. D. A. Shirley and B. J. Reeves, J. Organometallic Chem., 1969, 16, 1
18. E. J. Corey and D. Seebach, J. Org. Chem., 1966, 31, 4097
19. D. Seebach and A. K. Beck, Angew. Chem. Internat. Edn., 1974,13, 806
20. A. Anciaux, A. Eman, W. Dumont, and A. Krief, Tetrahedron Letters, 1975, 1617.
21. G. A. Russell and G. J. Mikol, J. Amer. Chem. Soc., 1966, 88, 5498
22. P. G. Gassman and G. D. Richmond, J. Org. Chem., 1966, 31.2355.
23. P. A. Grieco and C. J. Wang, J.C.S. Chem. Comm., 1975, 714.
24. R. M. Coates, Angew. Chem. Internat. Edn., 1973, 12, 586
25. R. M. Coates, H. D. Pigott, and J. Ollinger, Tetrahedron Letters, 1974, 3955
26. R. F. Romanet and R. H. Schlessinger, J. Amer. Chem. Soc., 1974, 96, 3701.
27. R. G. Pearson, Adv. Linear Free Energy Relationships, 1972, 281.
28. A. Delisle, Annalen, 1890, 260, 250
29. E. E. Reid, ‘Organic Chemistry of Bivalent Sulphur,’ Chemical Publishing Co. Inc. New York, 1960, vol. 2, p. 299.
30. J. F. Biellmann and J. B. Ducep, Tetrahedron Letters, 1968, 5629.
31. J. F. Biellmann and J. B. Ducep, H. J. Reich, J. Org. Chem., 1975, 40, 2570.
32. P. Brownbridge and S. Warren, J.S. Perkin I, 1976, 2125.
33. A. H. Davidson, I. Fleming, J. I. Grayson, A. Pearce, R. L. Snowden, and S. Warren, J.C.S. Perkin I, 1977, 550.
34. D. N. Jones, J. Blenkinsopp, A. C. F. Edmonds, E. Helmv, and R. J. K. Taylor, J.C.S. Perkin I, 1973, 2602
35. H. O. House, ‘Modern Synthetic Reactions,’ Benjamin, Menlo Park, 1972, 2nd edn., pp. 459-478.
36. M. Makosza, Pure Appl. Chem., 1975, 43, 439
37. M. Makosza, E. Bialecka, and M. Ludwikow, Tetrahedron Letters, 1972, 2391.
38. A. H. Davidson and S. Warren, J.C.S. Chem. Comm., 1976. 181.
39. J. F. Biellmann and J. B. Ducep, Tetrahedron Letters, 1969, 3707
40. J. F. Biellmann and J. B. Ducep Tetrahedron, 1971, 27, 5861
41. E. E. van Tamelen, R. A. Holton, R. E. Hopla, and W. E. Konz, J. Amer. Chem. Soc., 1972, 94, 8228, 8229
42. E. E. van Tamelen, P. McCurry, and U. Huber, Proc. Nat. Acad. Sci. U.S.A., 1971, 88, 1294
43. J. Hartmann, R. Muthukrishnan, and M. Schlosser, Helv. Chim. Acta, 1974, 57, 2261
44. K. Mori, M. Ohki, and M. Matsui, Tetrahedron, 1974, 30, 715
45. K. Kondo and M. Matsumoto, Tetrahedron Letters, 1976, 391
46. K. Oshima, K. Shimoji, H. Takahashi, H. Yamamoto, and H. Nozaki, J. Amer. Chem. Soc., 1973, 95, 2693
47. K. Oshima, H. Yamamoto, and H. Nozaki, J. Amer. Chem. Soc., p. 4446.
48. P. M. Atlani, J. F. Biellmann, S. Dube, and J. J. Vicens, Tetrahedron Letters, 1974, 2665.
49. P. L. Stotter and R. E. Hornish, J. Amer. Chem. Soc., 1973, 95, 4444
50. T. Nakai, H. Shiono, and M. Okawara, Tetrahedron Letters, 1975, 4027
51. K. Kondo, K. Matsui, and A. Negishi, Chem. Letters, 1974, 1371.
52. K. Oshima, H. Yamamoto, and H. Nozaki, J. Amer. Chem. Soc., 1973, 95, 7926.
53. D. A. Evans, Personal communication.
54. I. Fleming, Chem. And Ind., 1975, 449
55. E. Block, J. Chem. Educ., 1971, 48, 814.
56. A. J. Mura, G. Majetich, P. A. Grieco, and T. Cohen, Tetrahedron Letters, 1975, 4437, and references therein.
57. P. Blatcher, J. I. Grayson, and S. Warren, J.C.S. Chem. Comm., 1976, 547.
58. P. Brownbridge, I. Fleming, A. Pearce, and S. Warren, J.C.S. Chem. Comm., 1976, 751.
59. B. M. Trost, D. Keeley, and M. J. Bogdanowicz, J. Amer. Chem. Soc., 1973, 95, 3068
60. B. M. Trost and D. E. Keeley, J. Amer. Chem. Soc., 1974, 96, 1252
61. B. M. Trost, M. J. Bogdanowicz, and J. Kern, J. Amer. Chem. Soc., 1975, 97, 2218
62. B. M. Trost, Pure Appl. Chem., 1975, 43, 563.
63. P. Brownbridge and S. Warren, unpublished observations.
64. A. Delisle, Annalen, 1890, 260, 250.
65. E. A. Fehnel and M. Carmack, J. Amer. Chem. Soc., 1949, 71, 84.
66. E. G. G. Werner, Rec. Trav. chim., 1949, 68, 509.
67. A. A. Oswald, K. Griesbaum, W. A. Thaler, and B. E. Hudson, J. Amer. Chem. Soc., 1962, 84, 3897.
68. R. Dijkstra and H. J. Backer, Rec. Trav. chim., 1954, 73, 569.
69. Z. Ejmocki and Z. Eckstein, Roczniki Chem., 1971, 45, 345.
70. P. Bruin, A. F. Bickel, and E. C. Kooyman, Rec. Trav. chim., 1952, 71, 1115.
71. J. A. Marshall, N. H. Andersen, and J. W. Schlicher, J. Org. Chem., 1970, 35, 858.
72. M. Fieser and L. F. Fieser, ‘Reagents for Organic Synthesis,’ Wiley, New York, 1967, vol. 1, p. 1000.
73. D. D. MacNicol and J. J. McKendrick, J.C.S. Perkin I, 1974, 2493.
74. T. L. Jacobs and G. E. Illingworth, J. Org. Chem., 1963, 28, 2692
75. W. E. Parham and L. D. Edwards, J. Org. Chem., 1968, 33, 4150.
76. N. J. Leonard and C. R. Johnson, J. Org. Chem., 1962, 27, 282
77. A. J. Fatiadi, Synthesis, 1974, 229.
78. L. Li and W. H. Elliott, J. Amer. Chem. Soc., 1952,74,4089.
79. D. A. Evans, G. C. Andrews, and C. L. Sims, J. Amer. Chem. Soc., 1971, 93, 4956
80. P. A. Grieco, J.C.S. Chem. Comm., 1972, 702.
81. M. Schlosser and D. Coffinet, Synthesis, 1972, 575
82. M. Schlosser, Personal communication.
83. E. A. Braude and E. A. Evans, J. Chem. Soc., 1956, 3333.
84. B. C. Mayo, Chem. Soc. Rev., 1973, 2, 49.