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85022586647
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0001361552
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34548774476
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For elegant labeling studies of this system, see: d
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For elegant labeling studies of this system, see: d) B. M. M. Wheatley, B. A. Keay, J. Org. Chem. 2007, 72, 7253-7259.
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a) A. Sivaramakrishna, H. Su, J. R. Moss, Organometallics 2007, 26, 5786-5790;
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0012049250
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e) H. Matstj-zaka, Y. Hiroe, M. Iwasaki, Y. Ishii, Y. Koyast, M. Hidai, Chem. Lett. 1988, 377-380;
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f) D. V. Krupenya, S.I. Selivanov, S. P. Tunik, M. Haukka, T. A. Pakkanen, Dalton Trans. 2004, 2541-2549;
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g) E. Royo, S. Acebrön, M. E. G Mosquera, P. Royo, Organometallics 2007, 26, 3831-3839;
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h) G Chahboun, C. E. Petrisor, E. Gómez-Bengoa, E. Royo, T. Cuenca, Eur. J. Inorg. Chem. 2009, 1514-1520;
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37349060037
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i) A. Sivaramakrishna, B. C. E. Makhubela, F. Zheng, H. Su, G. S. Smith, J. R. Moss, Polyhedron 2008, 27, 44-52;
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42649130389
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j) A. Sivaramakrishna, P. Mushonga, I. L. Rogers, F. Zheng, R. J. Haines, E. Norlander, J. R. Moss, Polyhedron 2008, 27, 1911-1916;
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k) T. Mahamo, F. Zheng, A. Sivaramakrishna, J. R. Moss, G. Smith, J. Organomet. Chem. 2008, 693, 103-108;
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Mahamo, T.1
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22
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l) F Zheng, A. Sivaramakrishna, J. R. Moss, Inorg. Chim. Acta 2008, 361, 2871-2878.
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Zheng, F.1
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23
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70349967601
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The temporal fractional conversion should in fact be concentration independent. There is also an induction period evident with 1 (R - butenyl), see Figure 4 in reference [4a].
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The temporal fractional conversion should in fact be concentration independent. There is also an induction period evident with 1 (R - butenyl), see Figure 4 in reference [4a].
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25
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70349969428
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6, OTs, or OAc failed. Ts-4-toluenesulfonyl.
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6, OTs, or OAc failed. Ts-4-toluenesulfonyl.
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26
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55549096037
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L. A. Evans, N. Fey, J. N. Harvey, D. Hose, G. C. Lloyd-Jones, P. Murray, A. G Orpen, R. Osborne, G. J. Owen-Smith, M. Purdie, J. Am. Chem. Soc. 2008, 130, 14471-14473.
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Evans, L.A.1
Fey, N.2
Harvey, J.N.3
Hose, D.4
Lloyd-Jones, G.C.5
Murray, P.6
Orpen, A.G.7
Osborne, R.8
Owen-Smith, G.J.9
Purdie, M.10
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27
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70349973349
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-1) arises from interactions between the terminal methyl group and the approaching allyl group in 6, see the Supporting Information.
-
-1) arises from interactions between the terminal methyl group and the approaching allyl group in 6, see the Supporting Information.
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-
-
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28
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70349975605
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2O) and 720420 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
-
2O) and 720420 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
-
-
-
-
29
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70349957906
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2O were the most efficient but varied substantially from batch to batch, even though the addition of NaF or TBAF to reactions conducted in the presence of TfOH had no effect. TBAF = tetra-n-butylammonium fluoride.
-
2O were the most efficient but varied substantially from batch to batch, even though the addition of NaF or TBAF to reactions conducted in the presence of TfOH had no effect. TBAF = tetra-n-butylammonium fluoride.
-
-
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30
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7544222924
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E. S. Stoyanov, K.-C. Kim, C. A. Reed, J. Phys. Chem. A 2004, 108, 9310-9315.
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(2004)
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Stoyanov, E.S.1
Kim, K.-C.2
Reed, C.A.3
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32
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70349956374
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Preliminary DFT studies of intramolecular mechanisms identified feasible intermediates for B and C (12 and 13 kcalmol-1 above 4, but the calculated barriers in excess of 40 kcalmol-1 for C, D, and E would not be energetically accessible under the general reaction conditions 21°C, and no suitable transition state was located for pathway B. See the Supporting Information for a discussion
-
-1 for C, D, and E would not be energetically accessible under the general reaction conditions (21°C), and no suitable transition state was located for pathway B. See the Supporting Information for a discussion.
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33
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33745045979
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a) P. Drozdzewski, M. Musiala, M. Kubiak, Aust. J. Chem. 2006, 59, 329-335;
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Aust. J. Chem
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Drozdzewski, P.1
Musiala, M.2
Kubiak, M.3
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35
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70349956390
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See the Supporting Information for additional reactions of 4, and analogues, that reinforce this conclusion
-
See the Supporting Information for additional reactions of 4, and analogues, that reinforce this conclusion.
-
-
-
-
36
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70349961393
-
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Complexes tested: Z = diethyl, ethyl methyl, and di(tert-butyl) malonate, N-tosylamide, 4′,4′-dimethyl-3′,5′- dioxan-2′,6′-dionyl, and 3′,5′-dioxan-4-onyl. See the Supporting Information.
-
Complexes tested: Z = diethyl, ethyl methyl, and di(tert-butyl) malonate, N-tosylamide, 4′,4′-dimethyl-3′,5′- dioxan-2′,6′-dionyl, and 3′,5′-dioxan-4-onyl. See the Supporting Information.
-
-
-
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37
-
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0035477778
-
-
2H transfers are reminiscent of a palladium-catalyzed diene cycloisomerization mediated by a Pd(H) species that has been generated in situ. Such reactions commonly display induction periods and pseudo zero-order substrate dependency: a) K. L. Bray, I. J. S. Fairlamb, J. P. H. Charmant, G. C. Lloyd-Jones, Chem. Eur. J. 2001, 7, 4205-4215;
-
2H transfers are reminiscent of a palladium-catalyzed diene cycloisomerization mediated by a Pd(H) species that has been generated in situ. Such reactions commonly display induction periods and pseudo zero-order substrate dependency: a) K. L. Bray, I. J. S. Fairlamb, J. P. H. Charmant, G. C. Lloyd-Jones, Chem. Eur. J. 2001, 7, 4205-4215;
-
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38
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0002448834
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b) K. L. Bray, I. J. S. Fairlamb, J.-P. Kaiser, G. C. Lloyd-Jones, P. A. Slatford, Top. Catal. 2002, 19, 49-59;
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Bray, K.L.1
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33845193996
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d) K. L. Bray, G. C. Lloyd-Jones, M. P. Muñoz, P. A. Slatford, E. H. P. Tan, A. R. Tyler-Mahon, P. A. Worthington, Chem. Eur. J. 2006, 12, 8650-8663;
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0344012078
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f) L. A. Goj, G. A. Cisneros, W. Yang, R. A. Widenhoefer, J. Organomet. Chem. 2003, 687, 498-507.
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43
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6044274630
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3SiH resulted in no significant change over 12 h.
-
3SiH resulted in no significant change over 12 h.
-
-
-
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44
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70349941067
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TfOH may also generate the active catalyst 10 from 4, for example by demethylative lactonization (see reference [12]) then β-hydride elimination at C6. Despite careful GCMS/NMR analysis, we were unable to identify any coproducts from this process.
-
TfOH may also generate the active catalyst 10 from 4, for example by demethylative lactonization (see reference [12]) then β-hydride elimination at C6. Despite careful GCMS/NMR analysis, we were unable to identify any coproducts from this process.
-
-
-
-
45
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70349948745
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1H scrambling between C8 and C9.
-
1H scrambling between C8 and C9.
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