Abstract
Aniline reacts with variety of aryl aldehydes in ethanol to afford the corresponding imines. The reaction of imines with tris(dimethylsilyl)methyl lithium, (HMe2Si)3CLi, in THF at − 10°C gives 1,1-bis(silyl)-1-alkenes derivatives bearing Si-H functional and reactive groups.
Similar content being viewed by others
References
Colvin E (1988) Silicon reagents in organic synthesis. Academic Press, London
Patai S, Rappoport Z (1988) The chemistry of organosilicon compounds. Wiley, Chichester, England
Inoue A, Kondo J, Shinokubo H, Oshima K (2002) Chem Commun 2:114
Inoue A, Kondo J, Shinokubo H, Oshima K (2001) J Am Chem Soc 123:11109
Hodgson D, Comina P, Drew M (1997) J Chem Soc Perkin Trans 1:2279
Hodgson D, Comina P (1996) J Chem Commun 6:755
Jankowski P, Pleśniak K (2003) J Org Lett 5:2789
Gröbel B, Seebach D (1977) Chem Ber 110:852
Fleming I, Floyd D (1981) J Chem Soc Perkin Trans 1:969
Fleming I, Ghosh U (1994) J Chem Soc Perkin Trans 1:257
Narasaka K, Saito N, Hayashi Y, Ichida H (1990) Chem Lett 1411
Negishi E, Boardman L, Sawada H, Bagheri V (1988) J Am Chem Soc 110:5383
Flann C, Malone T, Overman L (1987) J Am Chem Soc 109:6097
Blumenkopf T, Overman L (1986) Chem Rev 86:857
Inoue A, Kondo J, Shinokubo H, Oshima K (2001) Chem Lett 10:956
Kondo J, Inoue A, Shinokubo H, Oshima K (2002) Tetrahedron Lett 43:2399
Safa K, Hassanpour A, Tofangdarzadeh S (2008) J Organomet Chem 693:3622
Safa K, Hassanpour A, Tofangdarzadeh S (2009) Synthetic communications 9:1601
International union of pure and applied chemistry. “imines”. Compendium of Chemical Terminology Internet edition
March Jerry (1985) Advanced Organic Chemistry reactions, mechanisms and structure, 3rd edn. John Wiley & Sons, New York: ISBN 0-471-85472-7
Fletcher, Dermer, Fox (1974) Nomenclature of Organic Compounds
Patai S (1970) The chemistry of the carbon–nitrogen double bond. Wiley, London
Patai S (1968) The chemistry of the amino group. Wiley, London
Patai S (1966) The chemistry of the carbonyl group. Wiley, London
Layer R (1963) Chem Rev 63:489
Goering B (1955) Ph.D. Dissertation, Cornell University
Otto S (2006) Chem Rev 106:3652
Meyer C, Joiner C, Stoddart J (1705) Chem Soc Rev 36:1705
Rowan S, Cantrill S, Cousins G (2002) Angew Chem 114:938
Storm O, Lüning U (2002) Chem Eur J 8:793
Hawrelak E, Ladipo F, Sata D (1999) Organometallics 18:1804
Shibata I, Kawakami T, Tanizawa D (1998) J Org Chem 63:383
Author information
Authors and Affiliations
Corresponding author
Electronic Supplementary Material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Oskoei, Y.M., Mousavi-azar, A., Madram, A. et al. A New Facile One-Pot Method for Preparation of 1,1-bis(silyl)alkene Via Imine Precursor. Silicon 4, 251–257 (2012). https://doi.org/10.1007/s12633-012-9128-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12633-012-9128-9