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Tetrahedron Letters

Volumn 17, Issue 31, 1976, Pages 2667-2670

Cleavage of the silicon-carbon bond by fluoride ion in triorganosilyloxiranes. The stereochemistry of substitution at oxiranyl carbon.

(3) Chan, T H a Lau, P W K a Li, M P a

a MCGILL UNIVERSITY (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000922004 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)77790-2 Document Type: Article

Times cited : (86)

References (23)

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8
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9
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10
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- On isolation by TLC, a mixture of triphenylfluorosilane and triphenylsilanol was obtained.

11
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- 2 gas through the reaction mixture. Its identity was established by pmr comparison with authentic sample.

12
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- Prepared by the epoxidation of E-1-phenyl-2-trimethylsilylethylene which was synthesized according to D. Seyferth, L.G. Vaughan and R. Suzuki, J. Organometal. Chem., 1 444 (1964).

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- 15.

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- Determination oferythroandthreoconfigurations by nuclear magnetic resonance spectroscopy
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- Eclipsing conformation has been found to be general for alkenes. See, E.L. Eliel, N.L. Allinger, Wiley-Interscience, New York
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- Karabatsos¹ Fenoglio²

17
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- Epoxidation of allylic alcohols with peroxy-acids. Attempts to define transition state geometry
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18
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- The proton trans- to the phenyl group in styrene oxide was assigned by C.A. Reilly and J.D. Swalen, J. Chem. Phys., 32, 1378 (1960). In the present case, p.m.r. integration gave the relative rations of the trans-proton, the cis-proton and the benzylic proton, as 0.67/1.00/1.00. The modest deuterium incorporation was due in part to the trace of water inevitably present in tetraethylammonium fluoride.

19
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21
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- Also the review by, A. Weissberger, Interscience, New York
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22
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- Influence of steric factors on the rates of thermal racemisation of N-alkyl-oxaziridines. Isolation of an enantiomer whose optical activity is due solely to a tercovalent asymmetric nitrogen atom
- Inversion barrier for the nitrogen pyramid of the isoelectronic oxaziridine was found to be high. See
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23
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