Acidity of Imidodicarbonates and Tosylcarbamates in Dimethyl Sulfoxide. Correlation with Yields in the Mitsunobu Reaction

Journal of Organic Chemistry

Volumn 56, Issue 25, 1991, Pages 7172-7174

  Koppel, Ilmar ^a,b   Koppel, Juta ^a,b   Degerbeck, Fredrik ^a,b   Grehn, Leif ^a,b   Ragnarsson, Ulf ^a,b  

^a UNIVERSITY OF TARTU   (Estonia)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001508823     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00025a041     Document Type: Note

References (32)

1. Carpino, L. A. J. Org. Chem. 1964, 29, 2820.
2. Grehn, L.; Ragnarsson, U. Synthesis 1987, 275.
3. Grehn, L.; Ragnarsson, U. Coll. Czech. Chem. Commun. 1988, 53, 2778.
4. Gibson, M. S.; Bradshaw, R. W. Angew. Chem. 1968, 80, 986.
5. Gibson, M. S.; Bradshaw, R. W. Angew. Chem., Int. Ed. Engl. 1968, 7, 919.
6. Ragnarsson, U.; Grehn, L. Acc. Chem. Res. 1991, 24, 285.
7. Mitsunobu, O. Synthesis 1981, 1.
8. Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235.
9. Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487.
10. Crich, D.; Dyker, H.; Harris, R. J. J. Org. Chem. 1989, 54, 257.
11. Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, Jr., G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
12. Degerbeck, F.; Fransson, B.; Grehn, L.; Ragnarsson, U. J. Chem. Soc., Perkin Trans. 1, in press.
13. Grehn, L.; Almeida, M. L. S.; Ragnarsson, U. Synthesis 1988, 992.
14. Bodanszky, M. Principles of Peptide Synthesis; Springer: Berlin, 1984; p 90.
15. Connell, R. D.; Rein, T.; Ökermark, B.; Helquist, P. J. Org. Chem. 1988, 53, 3845.
16. Weygand, F.; Hunger, K. Chem. Ber. 1962, 95, 1.
17. Erickson, B. W.; Merrifield, R. B. J. Am. Chem. Soc. 1973, 95, 3757.
18. Stevens, C. M.; Watanabe, R. J. Am. Chem. Soc. 1950, 72, 725.
19. Carpenter, F. H.; Gish, D. T. J. Am. Chem. Soc. 1952, 74, 3818.
20. Eckert, H.; Ugi, I. Angew. Chem. 1976, 88, 717.
21. Eckert, H.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1976, 15, 681.
22. Veber, D. F.; Brady, S. F.; Hirschmann, R. In Chemistry and Biology of Peptides; Meienhofer, J., Ed.; Ann Arbor Science Publishers: Ann Arbor, 1972; pp 315-319.
23. Veber, D. F.; Paleveda, W. J.; Lee, Y. C.; Hirschmann, R. J. Org. Chem. 1977, 42, 3286.
24. Woodward, R. B.; Heusler, K.; Gosteli, J.; Naegeli, P.; Oppolzer, W.; Ram age, R.; Ranganathan, S.; Vorbrüggen, H. J. Am. Chem. Soc. 1966, 88, 852.
25. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
26. Wada, M.; Mitsunobu, O. Tetrahedron Lett. 1972, 1279.
27. Milcent, R.; Guevrekian-Soghomoniantz, M.; Baibier, G. J. Heterocycl. Chem. 1986, 23, 1845.
28. Koppel, I. A.; Moretskaya, L. A.; Koppel, J. B.; Pihl, V. O. Org. React. (Tartu) 1977, 14, 81.
29. Koppel, I. A.; Moretskaya, L. A.; Lantvoyev, V. I.; Koppel, J. B.; Pihl, V. O. Org. React. (Tartu) 1983, 20, 508.
30. Koppel, I. A.; Koppel, J. B.; Pihl, V. O. Org. React. (Tartu) 1988, 25, 77.
31. Gyenes, I. Titration in Non-Aqueous Media; Van Nostrand: Princeton, NJ, 1967.
32. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1967, 89, 1721.