Synthetic Applications and Mechanism Studies of the Decarbalkoxylations of Geminal Diesters and Related Systems Effected in MeaSO by Water and/or by Water with Added Salts

Journal of Organic Chemistry

Volumn 43, Issue 1, 1978, Pages 138-147

  Krapcho, A Paul ^a   Weimaster, J F ^a   Eldridge, J M ^a   Jahngen, E G E ^a   Lovey, A J ^a   Stephens, W P ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947093954     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00395a032     Document Type: Article

References (83)

1. A. P. Krapcho, G. A. Glynn and B. J. Grenon, Tetrahedron Lett., 215 (1967.
2. M. Fieser and L. F. Fieser, “Reagents for Organic Synthesis”, Vol. 2, Wiley-lnterscience, New York, N.Y., p 381 (1969.
3. A. P. Krapcho and A. J. Lovey, Tetrahedron Lett., 957 (1973.
4. A. P. Krapcho, E. G. E. Jahngen, Jr., A. J. Lovey and F. W. Short, Tetrahedron Lett., 1091 (1974.
5. M. Fieser and L. F. Fieser, “Reagents for Organic Synthesis”, Vol. 5, Wiley-lnterscience, New York, N.Y., p 265 (1975.
6. C. L. Liotta and F. L. Cook, Tetrahedron Lett., 1095 (1974.
7. A. P. Krapcho and B. P. Mundy, Tetrahedron, 26, 5437 (1970.
8. a. J. Harley-Mason and Atta-ur-Rahman, Chem. Ind. (London), 1845 (1968.
9. W. S. Johnson, C. A. Harbert and R. D. Stipanovic, J. Am. Chem. Soc., 90, 5279 (1968.
10. W. S. Johnson, C. A. Harbert, B. E. Ratcliffe and R. D. Stipanovic, J. Am. Chem. Soc., 98, 6188 (1976.
11. F. Texier and R. Carrie, Bull. Soc. Chim. Fr 258 (1972.
12. E. J. Corey and H. A. Kirst, J. Am. Chem. Soc., 94, 667 (1972.
13. E. E. van Tamelen and R. J. Anderson, J. Am. Chem. Soc., 94, 8225 (1972.
14. E. E. van Tamelen, M. P. Seiler and W. Wierenga, J. Am. Chem. Soc., 94, 8229 (1972.
15. F. Collonges and G. Descotes, Tetrahedron Lett., 1117 (1973.
16. R. V. Venkateswaran, I. Gupta and P. K. Ghoshal, Indian J. Chem., Sect. B, 14, 243 (1976.
17. W. Kirmse, J. Knist and H.-J. Ratajczak, Chem. Ber., 109, 2296 (1976.
18. L. J. Dolby and H. Biere, J. Org. Chem., 35, 3843 (1970.
19. B. W. Peace and D. S. Wulfman, Synthesis, 137 (1973.
20. a. B. M. Trost and T. J. Dietsche, J. Am. Chem. Soc., 95, 8200 (1973.
21. B. M. Trost, T, J. Dietsche and T. J. Fullerton, J. Org. Chem., 39, 737 (1974.
22. B. M. Trost and L. Weber, J. Org. Chem., 40, 3617 (1975.
23. J. E. McMurry and G. B. Wong, Synth. Commun., 2, 389 (1972.
24. a. P. Muller and B. Siegfried, Tetrahedron Lett., 3565 (1973.
25. P. Muller and B. Siegfried, Heiv. Chim. Acta, 57, 987 (1974.
26. A. Greene and P. Crabbe, Tetrahedron Lett., 2215 (1975.
27. a. O. P. Vig, S. S. Bari, O. P. Sood and S. D. Sharma, Indian J. Chem., Sect. B, 14, 438(1976.
28. J. B. P. A. Wijnberg and W. N. Speckamp, Tetrahedron Lett., 4035 (19751.
29. a. P. Goswani, R. V. Venkateswaran and P. C. Dutta, Indian J. Chem., Sect. B, 14, 299 (1976.
30. S. Torii, H. Tanaka and T. Mandai, J. Org. Chem., 40, 2221 (1975.
31. P. M. McCurry and K. Abe, Tetrahedron Lett., 1387 (1974.
32. B. S. Huang, E. J. Parish and D. H. Miles, J. Org. Chem., 39,2647 (1974.
33. a. A. Bernhard, Justus Liebigs Ann. Chem., 282, 153 (1894.
34. D. S. Breslow, E. Baumgarten and C. R. Hauser, J. Am. Chem. Soc., 66, 1286 (1944.
35. J. B. Paine III, W. B. Kirshner, D. W. Moskowitz and D. Dolphin, J. Org. Chem., 41, 3857 (1976)
36. H. Meerwein, Justus Liebigs Ann. Chem., 398, 242 (1913)
37. H. Meerwein and W. Schurmann, Justus Liebigs Ann. Chem., 398, 196 (1913.
38. a. A. T. Nielsen and W, R. Carpenter, Org. Synth., 5, 288 (1973.
39. H. Musso and D. Dopp, Chem. Ber., 97, 1147 (1964.
40. J. R. Vincent, A. F. Thompson, Jr. and L. I. Smith, J. Org. Chem., 3, 603 (1939.
41. A. E. Greene, A. Cruz and P. Crabbe, Tetrahedron Lett., 2707 (1976)(1973)
42. J. R. Johnson and F. D. Hager, Org. Synth., 1, 351 (1944.
43. F. Elsinger, Org. Synth., 5, 76 (1973)
44. J. Kossanyi, B. Furth and J. P. Morizur, Tetrahedron Lett., 3459 (1973.
45. a. K. Kondo, T. Umemoto, Y. Takahatake and D. Tunemoto, Tetrahedron Lett., 113 (1977. b. D. Tunemoto, N. Araki and K. Kondo, Tetrahedron Lett., 109 (1977.
46. a. I. T. Harrison, V. R. Fletcher and J. H. Fried, Tetrahedron Lett., 2733(1974.
47. K. Kondo, E. Hiro and D. Tunemoto, Tetrahedron Lett., 4489 (1976.
48. a.D. Y. Chang, S. H. Lee and H. C. Lee, J. Org. Chem., 32, 3716 (1967.
49. D. Y. Chang, C. F. Yam, S. Y. Chan, S. H. Lee. and H. C. Lee, J. Org. Chem., 31, 3267(1966.
50. G. A. Smith and D. H. Williams, J. Chem. Soc. Perkin Trans. 1, 2811 (1972.
51. a. S. Takei and Y. Kawano, Tetrahedron Lett. 4389 (1975.
52. M. Asaoka, K. Miyake and H. Takei, Chemistry Lett., 1149 (1975.
53. J. J. Wilczynski and H. W. Johnson, Jr., J. Org. Chem., 39, 1909 (1974), obtained methyl acetate in a 35% yield.
54. E., S. Behare and R, B. Miller, J. Chem. Soc. D, 402 (1970.
55. a. F. Elsinger, J. Schreiber and A. Eschenmoser, Heiv. Chim. Acta, 43, 113 (1960)
56. P. D. G. Dean, J. Chem. Soc., 6655 (1965.
57. P. A. Bartlett and W. S. Johnson, Tetrahedron Lett., 4459 (1970.
58. P. Ykman and H. K. Hall, Jr., Tetrahedron Lett., 2429 (1975.
59. N. Ono, H. Eto, R. Tamura and J. Hayami, Chem. Lett., 757 (1976.
60. a. B. M. Trost and T. R. Verhoeven, J. Org. Chem., 41, 3215 (1976)
61. B. M. Trost and T. R. Verhoeven, J. Am. Chem. Soc., 98, 630 (1976.
62. F. B. Thole and J. F. Thorpe, J. Chem. Soc., 99, 2183, 2187 (1911.
63. C. K. Ingold and J. F. Thorpe, J. Chem. Soc., 115, 143 (1919.
64. A. C. Cope and S. M. McElvain, J. Am. Chem. Soc., 54, 4311, 4319 (1932.
65. D. H. Miles and B. S. Huang, J. Org. Chem., 41, 208 (1976),.
66. E. J. Parish, B. S. Huang and D. H. Miles, Synth. Commun., 5, 341 (1975.
67. F. Texier, E. Marchand and R. Carrie, Tetrahedron, 30, 3185 (1974.
68. T. M. Santosusso and D. Swern, J. Org. Chem., 41, 2762 (1976.
69. a. J. F. J. Engbersen and J. B. F. N. Engberts, J. Am. Chem. Soc., 97, 1563 (1975.
70. T. H. Fife and D. M. McMahon, J. Am. Chem. Soc., 91, 7481 (1969.
71. W. P. Jencks and J. Carriuolo, J. Am. Chem. Soc., 83, 1743 (1961.
72. a. C. K. Ingold, “Structure and Mechanism in Organic Chemistry”, 2nd ed, Cornell University Press, Ithaca, N.Y., 1969, p 1131. for a review of ester hydrolysis mechanisms
73. R. E. J. Talbot, J. Am. Chem. Soc., 209 (1972.
74. a. D. H. R. Barton and C. P. Forbes, J. Chem. Soc., Perkin Trans. 1, 1614 (1975.
75. D. H. R. Barton, B. J. Garner and R. H. Wightman, J. Chem. Soc., 1855 (1964.
76. K. Mori, M. Tominaga, T. Takigawa and M. Matsui, Synthesis, 790 (1973.
77. a. F. C. Chang and N. F. Wood, Tetrahedron Lett., 2969 (1964.
78. L.R.C. Barclay, N. D. Hall and G. A. Cooke, Can. J. Chem., 40, 1981 (1962.
79. J. F. Bunnett, M. M. Robison and F. C. Pennington, J. Am. Chem. Soc., 72, 2378 (1950.
80. C. A. Bunton, A. E. Comyns, J. Graham and J. R. Quayle, J. Chem. Soc., 3817 (1955.
81. a. R. F. Pratt and T. C. Bruice, J. Am. Chem. Soc., 92, 5956 (1970.
82. B. Holmquist and T. C. Bruice, J. Am. Chem. Soc., 91, 2993, 3003 (1969.
83. E. W. Thomas and T. I. Crowell, J. Org. Chem., 37, 744 (1972.