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Volumn 23, Issue 3, 1982, Pages 259-262

Silicon in organic syntheis. 13. The 1-trimethylsilylcyclopropyl anion and its formal equivalent

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EID: 49049131007 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)86803-3 Document Type: Article

Times cited : (22)

References (28)

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- Trost¹ Jungheim²

11
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- Paquette, L.A.; Wells, G.J.; Horn, K.A.; Yan, T.-H. following paper.

12
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- Vinyl Derivatives of Metals. XIV. Reaction of the Trimethylvinyl Compounds of Silicon, Germanium, and Tin with Iodomethylzinc Iodide. Preparation of Cyclopropyltin Compounds by the Grignard Procedure
- (1962) Inorganic Chemistry , vol.1 , pp. 913
- Seyferth¹ Cohen²

14
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- Professor R.F. Cunico has informed us of similar negative experiments in his laboratory.

15
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- This reagent/solvent combination is highly preferred for the deprotonation of trimethylsilane:
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 5004
- Ehlinger¹ Magnus²

18
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- (1979) Tetrahedron Lett. , vol.44 , pp. 3599
- Cohen¹ Gapinski² Hutchins³

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- Screttas¹ Micha-Screttas²

20
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- (1978) Tetrahedron Lett. , vol.43 , pp. 1064
- Screttas¹ Micha-Screttas²

21
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- A simple, highly versatile synthesis of cyclopropyl phenyl sulfides.
- (1980) Chemistry Letters , pp. 287
- Tanaka¹ Uneme² Matsui³ Tanikaga⁴ Kaji⁵

22
- 84919046260
- The feasibility of lithium 1-(dimethylamino)naphthalenide in the present context has also been examined, but with less satisfactory results (incomplete reduction). As noted by others [Bank, S.; Platz, M. Tetrahedron Lett., 2097; Cohen, T.; Matz, J.R. Synth. Commun., 10, 311], the aromatic byproduct can in this instance be separated from the carbinols by acid extraction.

23
- 84919046259
- α-Bromovinyltrimethylsilane [Chan, T.H.; Mychajlowskij, W.; Ong, B.S.; Harpp, D.N. J. Org. Chem., 43, 1526 is readily converted to the lithium reagent by the action of t-BuLi at −78°C in ether. Although earlier workers have utilized 1 equiv of t-BuLi for this purpose [Gröbel, B.-T.; Seebach, D. Angew. Chem., 86, 102; Chan, T.H.; Mychajlowskij, W. Tetrahedron Lett., 3479], we have noted that the use of 1.5 equiv improves the yield of carbinol by 14–20%.

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- Partial Asymmetric Synthesis in the Simmons-Smith Reaction. III. A Modification of the Reaction
- (1969) Bulletin of the Chemical Society of Japan , vol.42 , pp. 2669
- Sawada¹ Inoue²

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- Brown¹ Brewster² Shechter³

27
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- Silanes in organic synthesis. 10. Cleavage reactions of silylcyclopropanes with titanium tetrachloride and hydrogen chloride
- (1981) The Journal of Organic Chemistry , vol.49 , pp. 2901
- Compare Daniels¹ Paquette²

28
- 84919046256
- We thank the National Science Foundation and the National Institutes of Health for their financial support of this research.

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