Highly efficient desilylation of 3-trimethylsilylprop-2-ynamides by the action of KF-Al 2O 3

Russian Journal of Organic Chemistry

Volumn 47, Issue 12, 2011, Pages 1797-1801

  Andreev, M V ^a   Safronova, L P ^a   Medvedeva, A S ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84856257867     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1134/S1070428011120037     Document Type: Article

References (28)

1. D.L.J. Clive Y. Bo Y. Tao S. Daigneault Y.-J. Wu G. Meignan 1998 J. Am. Chem. Soc. 120 10 332 10.1021/ja980292s 1:CAS:528:DyaK1cXmtF2htrY%3D
2. P. Siemsen R.C. Livingston F. Diederich 2000 Angew. Chem., Int. Ed. 39 2632 10.1002/1521-3773(20000804)39:15<2632::AID-ANIE2632>3.0.CO;2-F 1:CAS:528:DC%2BD3cXmtFCjt7Y%3D
3. A.S. Medvedeva 1996 Russ. J. Org. Chem. 32 272
4. Pierce, A.E., Silylation of Organic Compounds. A Technique for Gas-Phase Analysis, Rockford: Pierce Chemical, 1968, p. 3.
5. S.J. Coats J.S. Link D. Gauthier D.J. Hlasta 2005 Org. Lett. 7 1469 10.1021/ol047637y 1:CAS:528:DC%2BD2MXisV2js78%3D
6. T. Nishinaga Y. Miyata N. Nodera K. Komatsu 2004 Tetrahedron 60 3375 10.1016/j.tet.2004.02.041 1:CAS:528:DC%2BD2cXisVGntLc%3D
7. P. Casara C. Danzin B. Metcalf M. Jung 1985 J. Chem. Soc., Perkin Trans. 1 2201 10.1039/p19850002201
8. A.L.K. Shi Shun R.R. Tykwinski 2003 J. Org. Chem. 68 6810 10.1021/jo034734g
9. De Meijere, A., Kozhushkov, S.I., Boese, R., Haumann, T., Yufit, D.S., Howard, J.A.K., Khaikin, L.S., and Trætteberg, M., Eur. J. Org. Chem., 2002, p. 485.
10. J.E.D. Kirkham T.D.L. Courtney V. Lee J.E. Baldwin 2004 Tetrahedron Lett. 45 5645 10.1016/j.tetlet.2004.05.122 1:CAS:528:DC%2BD2cXlt1ehsrc%3D
11. Tretyakov, E., Romanenko, G., Ikorskii, V., Stass, D., Vasiliev, V., Demina, M., Mareev, A., Medvedeva, A., and Ovcharenko, V., Eur. J. Org. Chem., 2007, p. 3639;
12. Tretyakov, E., Tolstikov, S., Mareev, A., Medvedeva, A., Romanenko, G., Stass, D., Bogomyakov, A., and Ovcharenko, V., Eur. J. Org. Chem., 2009, p. 2548.
13. Kabalka, G.W., Wang, L., and Pagni, R.M., Arkivoc, 2001, part (iv), p. 5.
14. Albert, A. and Serjeant, E., Ionization Constants of Acids and Bases, London: Methuen, 1962. Translated under the title Konstanty ionizatsii kislot i osnovanii, Moscow: Khimiya, 1964, p. 131.
15. T. Iida K. Hori K. Nomura E. Yoshii 1994 Heterocycles 38 1839 10.3987/COM-94-6751 1:CAS:528:DyaK2MXks1Kruw%3D%3D
16. G. Coppola R. Damon 1995 J. Heterocycl. Chem. 32 1141 10.1002/jhet.5570320407 1:CAS:528:DyaK2MXnvVyjtrw%3D
17. C. Kanner U. Pandit 1982 Tetrahedron 38 3597 10.1016/0040-4020(82)80066-5 1:CAS:528:DyaL3sXkslSmsbw%3D
18. Sánchez, V., Rebolledo, F., and Gotor, V., Synlett, 1994, p. 529.
19. Miller, L., US Patent no. 3 210 420, 1965;
20. Chem. Abstr., 1965, vol. 63, p. 17 971 h.
21. K. Undheim L. Riege 1975 J. Chem. Soc., Perkin Trans. 1 1493 10.1039/p19750001493
22. D. Duckworth S. Lee-Wong A. Slawin E. Smith D. Williams 1996 J. Chem. Soc., Perkin Trans. 1 815 10.1039/p19960000815
23. Raphael, R.A., Acetylenic Compounds in Organic Synthesis, New York: Academic, 1955.
24. L.P. Safronova A.S. Medvedeva N.S. Vyazankin 1983 Zh. Obshch. Khim. 53 1313 1:CAS:528:DyaL3sXlslGrt7s%3D
25. G. Coppola R. Damon 1993 Synth. Commun. 23 2003 10.1080/00397919308009860 1:CAS:528:DyaK2cXns1yktA%3D%3D
26. A.S. Medvedeva M.V. Andreev L.P. Safronova 2010 Russ. J. Org. Chem. 46 1466 10.1134/S1070428010100040 1:CAS:528:DC%2BC3cXhsVWhtLnL
27. V. Yadav K. Babu M. Mittal 2001 Tetrahedron 57 7047 10.1016/S0040- 4020(01)00677-9 1:CAS:528:DC%2BD3MXltlyrt7Y%3D
28. T. Ferris P. Lee T. Farrar 1997 Magn. Reson. Chem. 35 571 10.1002/(SICI)1097-458X(199709)35:9<571::AID-OMR140>3.0.CO;2-K 1:CAS:528:DyaK2sXlvFOhurg%3D