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0038092166
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The ring strain of the parent silirane has been calculated to be 44 kcal/mol: Gordon, M. S.; Nelson, W. Organometallics 1995, 14, 1067-1069.
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0001319615
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Fleming, I.1
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0000936121
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Ring opening of postulated silacyclopropene intermediates by MeOH, MeCHO, and acetone has been reported: Lee, S. T.; Baek, E. K.; Shim, S. C. Organometallics 1996, 15, 2182-2184.
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85033136122
-
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Thermal deuteriomethanolysis proceeded with the same stereochemical outcome, albeit with extensive decomposition
-
Thermal deuteriomethanolysis proceeded with the same stereochemical outcome, albeit with extensive decomposition.
-
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31
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0007623379
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For example, the 3-deuterio-2-butanols are known: Kabalka, G. W.; Bowman, N. S. J. Org. Chem. 1973, 38, 1607-1608.
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85033153063
-
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note
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Control experiments indicate that the products are formed kinetically and that no isomerization of the silirane occurred during either the thermal or catalyzed insertions.
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34
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0000276453
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33845278140
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3BH: Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
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47
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85033141845
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note
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1H NMR spectra of the major isomers 20a of the two substituted systems compared to that of 10a. Because the reactions were low-yielding, no further attempts were made to prove the stereochemistry.
-
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48
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85033134831
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The details are provided as Supporting Information
-
The details are provided as Supporting Information.
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49
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0347195435
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85033139031
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note
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Further confirmation of the stereochemistry of 27 was obtained by reductive amination of the corresponding primary diamine with benzaldehyde.
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54
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0001671575
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For reactions of silylenes with imines, see: (a) Weidenbruch, M.; Piel, H.; Peters, K.; von Schnering, H. G. Organometallics 1993, 12, 2881-2882. (b) Belzner, J.; Ihmels, H.; Pauletto, L.; Noltemeyer, M. J. Org. Chem. 1996, 61, 3315-3319.
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Weidenbruch, M.1
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0006298183
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For reactions of silylenes with imines, see: (a) Weidenbruch, M.; Piel, H.; Peters, K.; von Schnering, H. G. Organometallics 1993, 12, 2881-2882. (b) Belzner, J.; Ihmels, H.; Pauletto, L.; Noltemeyer, M. J. Org. Chem. 1996, 61, 3315-3319.
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Electrophilic attack of pentacoordinate silanes with electrophiles can occur with either retention or inversion of configuration: Tamao, K.; Yoshida, J.-i.; Yamamoto, H.; Kakui, T.; Matsumoto, H.; Takahashi, M.; Kurita, A.; Murata, M.; Kumada, M. Organometallics 1982, 1, 355-368.
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