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1
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0001363228
-
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Seyferth, D.; Duncan, D. P.; Shannon, M. L. Organometallics 1984, 3, 579-583 and references therein.
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Seyferth, D.1
Duncan, D.P.2
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2
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0007055948
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Seyferth, D.; Duncan, D. P.; Shannon, M. L.; Goldman, E. W. Organometallics 1984, 3, 574-578.
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Seyferth, D.1
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3
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Boudjouk, P.; Samaraweera, U.; Sooriyakumaran, R.; Chrusciel, J.; Anderson, K. R. Angew. Chem., Int. Ed. Engl. 1988, 27, 1355-1356.
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4
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0001319615
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Bodnar, P. M.; Palmer, W. S.; Shaw. J. T.; Smitrovich, J. H.; Sonnenberg, J. D.; Presley, A. L.; Woerpel, K. A. J. Am. Chem. Soc. 1995, 117, 10575-10576.
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5
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0001323039
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Bodnar, P. M.; Palmer, W. S.; Ridgway, B. H.; Shaw, J. T.; Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1997, 62, 4737-4745.
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7
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0029944027
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Kroke, E.; Willms, S.; Weidenbruch, M.; Saak, W.; Pohl, S.; Marsmann, H. Tetrahedron Lett. 1996, 37, 3675-3678.
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Kroke, E.1
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-
13
-
-
0344057358
-
-
note
-
Control experiments indicate that cis-1 is more thermally labile than trans-1.
-
-
-
-
14
-
-
0344488575
-
-
note
-
This formamide was used to simplify spectral analyses.
-
-
-
-
15
-
-
0345350946
-
-
note
-
1H NMR spectroscopy is most likely due to the presence of trans-2-butene as an impurity in commercially available cis-2-butene, from which silacyclopropane cis-1 was made. The typical purity of cis-1 is ≥95%.
-
-
-
-
16
-
-
0344488574
-
-
note
-
The stereochemistry of these products was proven rigorously. The details are provided as Supporting Information.
-
-
-
-
18
-
-
0344057357
-
-
note
-
The stereochemistries of insertion products derived from 8 were determined by analysis of NOE data. A summary of these data is provided as Supporting Information.
-
-
-
-
19
-
-
0002511383
-
-
Bleaching of the characteristic blue-green color of copper(II) salts was observed upon addition of the silacyclopropane. The reduction of palladium(II) salts with silacyclopropanes was demonstrated: Seyferth, D.; Shannon, M. L.; Vick, S. C.; Lim, T. F. O. Organometallics 1985, 4, 57-62.
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Seyferth, D.1
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Lim, T.F.O.4
-
20
-
-
0039659338
-
-
The reduction of copper(II) to copper(I) by pentafluorosiliconates was reported: Yoshida, J.-i.; Tamao, K.; Kakui, T.; Kurita, A.; Murata, M.; Yamada, K.; Kumada, M. Organometallics 1982, 1, 369-380.
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Yoshida, J.-I.1
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Kumada, M.7
-
21
-
-
0344919689
-
-
note
-
Use of 10 mol % CuI with crotonaldehyde led to a 64% yield of 10b as an 87:13 mixture of diastereomers; ZnBr2 afforded a 62% yield of an 87:13 mixture. An 87:13 mixture was observed for CuI-catalyzed insertion of tiglic aldehyde. These mixtures permitted comparison of NOE data between the major and minor diastereomers.
-
-
-
-
23
-
-
0032577035
-
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Lipshutz, B. H.; Sclafani, J. A.; Takanami, T. J. Am. Chem. Soc. 1998, 120, 4021-4022.
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24
-
-
0344057352
-
-
note
-
The connectivity of this structure was determined using COSY experiments.
-
-
-
-
25
-
-
0344057353
-
-
note
-
The stereochemistry of 18a was determined unambiguously (ref 5). The stereochemistries of 18b-d were assigned by analogy.
-
-
-
-
26
-
-
0024294399
-
-
For a review that includes the use of metal complexes to catalyze carbonyl additions, see: Evans, D. A. Science 1988, 240, 420-426.
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Evans, D.A.1
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0040251087
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Maitlis observed that weak Lewis acids catalyzed rearrangement reactions of cyclopropane-containing strained ring compounds: Kaiser, K. L.; Childs, R. F.; Maitlis, P. M. J. Am. Chem. Soc. 1971, 93, 1270-1272.
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0030008366
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Copper(II) salts lower the barrier to inversion of amides by preferential coordination to the amide nitrogen: Cox, C.; Ferraris, D.; Murthy, N. N. J. Am. Chem. Soc. 1996, 118, 5332-5333.
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-
-
0344057351
-
-
note
-
1H NMR signals of cis- and trans-2-butene are not well resolved in this solvent.
-
-
-
-
31
-
-
0001177017
-
-
This compound was identified on the basis of its spectral properties. The rapid hydrolysis of this dioxasilolane was reported by Corey: Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 4871-4874.
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Corey, E.J.1
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32
-
-
0344919688
-
-
note
-
When this transformation was performed starting at -78°C and the reaction solution was warmed to 22°C, dioxasilolane 21 was accompanied by 13% of cis-6 as a 63:37 ratio of diastereomers.
-
-
-
-
34
-
-
0000271118
-
-
Stable silylenes have been observed to effect dimerization of aldehydes to form dioxasilolane products: Jutzi, P.; Eikenberg, D.; Bunte, E.-A.; Möhrke, A.; Neumann, B.; Stammler, H.-G. Organometallics 1996, 15, 1930-1934.
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0001431584
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Seyferth, D.; Annarelli, D. C.; Duncan, D. P. Organometallics 1982, 1, 1288-1294.
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0345350590
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No deuteriomethanolysis was observed at 22°C in the absence of copper salts.
-
-
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40
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54149115435
-
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For some examples of the stereochemistry of transmetalation reactions, see: (a) Silicon to palladium: Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793-7794. (b) Tin to copper: Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982. Boron to palladium: Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 68, 458- 460. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461-470.
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For some examples of the stereochemistry of transmetalation reactions, see: (a) Silicon to palladium: Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793-7794. (b) Tin to copper: Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982. Boron to palladium: Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 68, 458- 460. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461-470.
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0000311321
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For some examples of the stereochemistry of transmetalation reactions, see: (a) Silicon to palladium: Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793-7794. (b) Tin to copper: Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982. Boron to palladium: Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 68, 458-460. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461-470.
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For some examples of the stereochemistry of transmetalation reactions, see: (a) Silicon to palladium: Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793-7794. (b) Tin to copper: Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982. Boron to palladium: Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 68, 458- 460. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461-470.
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