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1
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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
Duncan, D.P.2
Shannon, M.L.3
Goldman, E.W.4
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2
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0001363228
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and references therein
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Seyferth, D.; Duncan, D. P.; Shannon, M. L. Organometallics 1984, 3, 579-583 and references therein.
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Organometallics
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Seyferth, D.1
Duncan, D.P.2
Shannon, M.L.3
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4
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0000475062
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Saso, H.; Ando, W.; Ueno, K. Tetrahedron 1989, 45, 1929-1940.
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Tetrahedron
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Saso, H.1
Ando, W.2
Ueno, K.3
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5
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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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Tetrahedron Lett.
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, pp. 3675-3678
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Kroke, E.1
Willms, S.2
Weidenbruch, M.3
Saak, W.4
Pohl, S.5
Marsmann, H.6
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6
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0344491039
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Brook, A. G.; Saxena, A. K.; Sawyer, J. F. Organometallics 1989, 8, 850-852.
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Organometallics
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Brook, A.G.1
Saxena, A.K.2
Sawyer, J.F.3
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7
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0142111818
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Saso, H.; Yoshida, H.; Ando, W. Tetrahedron Lett. 1988, 29, 4747-4750.
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Tetrahedron Lett.
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Saso, H.1
Yoshida, H.2
Ando, W.3
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9
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0007054178
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Boudjouk, P.; Black, E.; Kumarathasan, R.; Samaraweera, U.; Castellino, S.; Oliver, J. P.; Kampf, J. W. Organometallics 1994, 13, 3715-3727.
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Organometallics
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Boudjouk, P.1
Black, E.2
Kumarathasan, R.3
Samaraweera, U.4
Castellino, S.5
Oliver, J.P.6
Kampf, J.W.7
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10
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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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Bodnar, P.M.1
Palmer, W.S.2
Shaw, J.T.3
Smitrovich, J.H.4
Sonnenberg, J.D.5
Presley, A.L.6
Woerpel, K.A.7
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11
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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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Bodnar, P.M.1
Palmer, W.S.2
Ridgway, B.H.3
Shaw, J.T.4
Smitrovich, J.H.5
Woerpel, K.A.6
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17
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0345353459
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-
note
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29Si NMR chemical shifts of 2 and 3 correlate to stereochemistry: the two cis products cis-2 and cis-3 have chemical shifts of 31.4 and 31.5 ppm, respectively, whereas the two trans products trans-2 and trans-3 have chemical shifts of 30.2 and 30.6 ppm, respectively.
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18
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0344491037
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note
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These results are in contrast to the one-or two-atom insertions of sulfur into silacyclopropanes 1, which are not stereospecific. Radical intermediates were suggested for those transformations (ref 9).
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-
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20
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0344059804
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note
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The stereochemistry about the imine is not known. Weidenbruch, in his studies of this reaction (ref 5), demonstrated by X-ray crystallography that an iminosilacyclobutane possessed the (Z)-stereochemistry.
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21
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0345353458
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note
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We have examined the relative energies of the imine form and enamine form computationally using ab initio methods (the Spartan program from Wavefunction, Inc., Irvine, CA was employed). These calculations indicate that the relative energies between the two forms depends on the level of substitution on the silicon and nitrogen atoms as well as the substitution on the two ring carbons. Therefore, we conclude that the driving force behind the tautomerization is steric in origin.
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23
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0344059803
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Okano, K.; Morimoto, T.; Sekiya, M. J. Chem. Soc., Chem. Commun. 1985, 119-120.
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(1985)
J. Chem. Soc., Chem. Commun.
, pp. 119-120
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Okano, K.1
Morimoto, T.2
Sekiya, M.3
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24
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0344922101
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-
note
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1H NMR spectroscopy and gas chromatography. This small amount of trans-dimethyl compound 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%.
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-
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25
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0031115798
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19F} NOE difference spectroscopy, see (a) Huber, E. W.; Kane, J. M.; Dalton, C. R. J. Fluorine Chem. 1997, 82, 47-50.
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(1997)
J. Fluorine Chem.
, vol.82
, pp. 47-50
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Huber, E.W.1
Kane, J.M.2
Dalton, C.R.3
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26
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0029655471
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(b) McCarthy, J. R.; Huber, E. W.; Le, T.-B.; Laskovics, F. M.; Matthews, D. P. Tetrahedron 1996, 52, 45-58.
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(1996)
Tetrahedron
, vol.52
, pp. 45-58
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-
McCarthy, J.R.1
Huber, E.W.2
Le, T.-B.3
Laskovics, F.M.4
Matthews, D.P.5
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27
-
-
0344491034
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-
note
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Homonuclear NOE experiments on 16 reveal a large NOE between the tert-butyl imino group and the C-4 methine and the hydroxyl group. These data are consistent with a conformation with both methyl groups and the trifluoromethyl group in axial positions, presumably to alleviate allylic strain.
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28
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0344922099
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note
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2 provided 10 and 11 in 66% overall yield from cis-3.
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-
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30
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84985631317
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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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(1988)
Angew. Chem., Int. Ed. Engl.
, vol.27
, pp. 1355-1356
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-
Boudjouk, P.1
Samaraweera, U.2
Sooriyakumaran, R.3
Chrusciel, J.4
Anderson, K.R.5
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31
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-
0344922097
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-
note
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Repeated attempts to obtain satisfactory elemental analysis were unsuccessful. Silicon carbide formation could prevent proper analyses.
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