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34
-
-
33750693484
-
-
note
-
Casey has prepared this complex in a very similar way; see ref 13.
-
-
-
-
35
-
-
33750698018
-
-
note
-
Except for very electron-rich N-alkyl imines, which formed thermostable ruthenium amine complexes that inhibited further catalysis.
-
-
-
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36
-
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0030984352
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(a) Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
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37
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0032706359
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(b) Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580.
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0033999757
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(c) Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466.
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Yamakawa, M.1
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-
40
-
-
33750725190
-
-
note
-
However with a methyl group on the nitrogen, an amine complex was observed.
-
-
-
-
41
-
-
0000007444
-
-
Abed, M.; Goldberg, I.; Stein, Z.; Shvo, Y. Organometallics 1988, 7, 2054.
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Abed, M.1
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42
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-
33750726834
-
-
Dissertation, Stockholm University
-
Samec, J. S. M. Dissertation, Stockholm University, 2005.
-
(2005)
-
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Samec, J.S.M.1
-
43
-
-
33750695397
-
-
note
-
When the reaction was run in THF-dg the complex appeared as diastereomeres with doublets at δ 0.88 and 0.92; both had a coupling constant of J = 6.5 Hz.
-
-
-
-
45
-
-
33750718576
-
-
note
-
Seven and six different experiments, respectively, were run for RuHOH and RuDOD individually.
-
-
-
-
46
-
-
33750714150
-
-
note
-
Casey's group has also performed a kinetic isotope study on different aldimines and found that very electron-deficient imines behave as aldehydes and electron-rich imines give inverse isotope effects. See ref 15.
-
-
-
-
47
-
-
33750726167
-
-
note
-
It has been established that dehydrogenation of amine 4 is much slower than hydrogen transfer from hydride 2 to the quinone when an excess of quinone is used. Furthermore, the former dehydrogenation step is an irreversible step under these conditions.
-
-
-
-
48
-
-
33750714505
-
-
note
-
When the α-carbon is deuterated in amine 4, the transfer of N-H and N-D will both be fast in relation to C-D cleavage and cannot be distinguished. On the other hand when the α-carbon is nondeuterated, the α-carbon-hydrogen bond cleavage is >3 times faster compared to the deuterated case and the difference in rate between transfer of the N-H and N-D can be partly seen.
-
-
-
-
49
-
-
33750738313
-
-
note
-
It was not possible to detect any free amine PhCH(Me)NHMe from reduction of imine 14 in the NMR spectrum.
-
-
-
-
50
-
-
33750691440
-
-
note
-
13C NMR for detection of 3 in 2 (see Supporting Information). However, the detection limit of the dimer is about 2%. With 2% of 3 up to ca. 4% of trapping complex could be formed.
-
-
-
-
51
-
-
84961986772
-
-
2 elimination from 2. See: Casey, C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am. Chem. Soc. 2005, 127, 3100.
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Casey, C.P.1
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Singer, S.W.3
Cui, Q.4
-
52
-
-
33750734010
-
-
note
-
10 = cyclohexylidene) with 2 gave a signal at δ -297 ppm.
-
-
-
-
53
-
-
33750731720
-
-
note
-
To confirm that this signal was not a protonated form of 18 a control experiment was run where the imine was mixed with TFA; no signal at δ -296 ppm was observed.
-
-
-
-
54
-
-
0012462507
-
-
Casey, C. P.; Bikzhanova, G. A.; Bäckvall, J.-E.; Johansson, L.; Park, J.; Kim, Y. H. Organometallics 2002, 21, 1955.
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Casey, C.P.1
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Bäckvall, J.-E.3
Johansson, L.4
Park, J.5
Kim, Y.H.6
-
55
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19744370551
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(a) Guan, H.; Iimura, M.; Magee, M. P.; Norton, J. R.; Zhu, G. J. Am. Chem. Soc. 2005, 127, 7805.
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Guan, H.1
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-
58
-
-
33750730011
-
Ionic hydrogenations
-
de Vries, J. G., Eds.; Elsevier, C. J.: in press (ISBN 3-527-31161-0)
-
(d) Bullock R. M. Ionic Hydrogenations. In Handbook of Homogeneous Hydrogenation; de Vries, J. G., Eds.; Elsevier, C. J.: in press (ISBN 3-527-31161-0).
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Bullock, R.M.1
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59
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21044443212
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(a) Martín-Matute, B.; Edin, M.; Bogár, K.; Kaynak, F. B.; Bäckvall, J. E. J. Am. Chem. Soc. 2005, 127, 8817.
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Martín-Matute, B.1
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60
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4344644257
-
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(b) Csjernyik, G.; Bogár, K.; Bäckvall, J.-E. Tetrahedron Lett. 2004, 45, 6799.
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Csjernyik, G.1
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0000102533
-
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Habib, A.; Tanke, R. S.; Holt, E. M.; Crabtree, R. H. Organometallics 1989, 8, 1225.
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-
Habib, A.1
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Crabtree, R.H.4
-
62
-
-
33750723878
-
-
note
-
For some of the intermediate structures, but not the TS. One single THF molecule was added.
-
-
-
-
63
-
-
33750738159
-
-
Submitted for publication
-
The calculations will be presented in a separate paper: Privalov, T.; Samec, J. S. M.; Bäckvall, J. E. Submitted for publication.
-
-
-
Privalov, T.1
Samec, J.S.M.2
Bäckvall, J.E.3
-
64
-
-
33644552723
-
-
Hydrogen was found to be predominantly trans to the imine (see also refs 15 and 16): Casey, C. P.; Bikzhanova, G. A.; Guzei, I. A. J. Am. Chem. Soc. 2006, 128, 2286.
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Casey, C.P.1
Bikzhanova, G.A.2
Guzei, I.A.3
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