Abstract
The electron rich C-C double bond of silyl enol ethers readily reacts with electrophilic carbenes to yield silyloxycyclopropanes. These are highly reactive compounds due to the cyclopropyl ring strain.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Simmons, H.E., Smith, R.D.: J. Am. Chem. Soc. 80, 5223 (1958)
Simmons, H.E., Smith, R.D.: J. Am. Chem. Soc. 81, 4256 (1959)
Denis, J.M., Girard, C., Conia, J.M.: Syn. 549 (1972)
Murai, S., Aya, T., Sonoda, N.: J. Org. Chem. 38, 4354 (1973)
Rubottom, G.M., Lopez, M.I.: J. Org. Chem. 38, 2097 (1973)
Conia, J.M., Girard, C.: Tetrahedron Lett. 2767 (1973)
Ryu, I., Murai, S., Otani, S., Sonoda, N.: Chem. Lett. 93, (1976)
Girard, C., Conia, J.M.: Tetrahedron Lett. 3333 (1974)
Girard, C., Conia, J.M.: Tetrahedron Lett. 3327 (1974)
Girard, C., Amice, P., Barnier, J.P., Conia, J.M.: Tetrahedron Lett. 3329 (1974)
Trost, B.M., Bogdanowicz, M.J.: J. Am. Chem. Soc. 95, 5311 (1973)
Trost, B.M., Scudder, P.H.: J. Org. Chem. 46, 506 (1981)
For a review of the rearrangement of vinyl cyclopropanes to cyclopentenes see: Rearrangements in Small Ring Compounds by Breslow, R., in Molecular Rearrangements (de Mayo, P., Ed.) Vol. I. pp. 234–245, New York: Interscience Publishers, 1963
Monti, S., Cowherd, F.G., McAninch, T.W.: J. Org. Chem. 40, 858 (1975)
Ryu, I., Murai, S., Otani, S., Sonoda, N.: Tetrahedron Lett. 1995 (1977)
Murai, S., Aya, T., Renge, T., Ryu, I., Sonoda, N.: J. Org. Chem. 39, 858 (1974)
Ryu, I., Murai, S., Sonoda, N.: Tetrahedron Lett. 4611 (1977)
Ito, Y., Saegusa, T.: J. Org. Chem. 42, 2326 (1977)
Murai, S., Seki, Y., Sonoda, N.: J. Chem. Soc., Chem. Commun. 1032 (1974)
Ryu, I., Matsumoto, K., Ando, M., Murai, S., Sonoda, N.: Tetrahedron Lett. 4283 (1980)
Rubottom, G.M., Marrero, R., Krueger, D.S., Schreiner, J.L.: Tetrahedron Lett. 4013 (1977)
Ito, Y., Fujii, S., Saegusa, T.: J. Org. Chem. 41, 2073 (1976)
Stork, G., MacDonald, T.L.: J. Am. Chem. Soc. 97, 1264 (1975)
Amice, P., Blanco, L., Conia, J.M.: Syn. 196 (1976)
Blanco, L., Amice, P., Conia, J.M.: Syn. 289 (1981)
Blanco, L., Amice, P., Conia, J.M.: Syn. 291 (1981)
Blanco, L., Slougui, M., Rousseau, G., Conia, J.M.: Tetrahedron Lett. 645 (1981)
Reissig, H.U., Hirsch, E.: Angew. Chem. Int. Ed. 19, 813 (1980)
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1983 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Weber, W.P. (1983). Cyclopropanation of Silyl Enol Ethers, Chemistry of Trimethylsilyloxycyclopropanes. In: Silicon Reagents for Organic Synthesis. Reactivity and Structure Concepts in Organic Chemistry, vol 14. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68661-0_14
Download citation
DOI: https://doi.org/10.1007/978-3-642-68661-0_14
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-68663-4
Online ISBN: 978-3-642-68661-0
eBook Packages: Springer Book Archive