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Lead references to Rh-catalyzed alkyne insertion: (a) Padwa, A. J. Organomet. Chem. 2001, 617, 3.
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(b) Padwa, A.; Krumpe, K. E.; Kassir, J. M. J. Org. Chem. 1992, 57, 4940.
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For an example of Rh-catalyred tandem intramolccular/intermolecular alkyne insertion, see ref 3d
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(a) For an example of Rh-catalyred tandem intramolccular/intermolecular alkyne insertion, see ref 3d.
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13
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33846067519
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Hoye has presented evidence that alkenyl carbenes may not be intermediates in intramolecular alkyne insertions. See ref 3c
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(b) Hoye has presented evidence that alkenyl carbenes may not be intermediates in intramolecular alkyne insertions. See ref 3c.
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(a) Baird, M. S. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1996; Vol. E17d, p 2695-2744.
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Lead references to catalytic cnantioselective cyclopropenations: (d) Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492.
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Lead references to catalytic cnantioselective cyclopropenations: (d) Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492.
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For the Rh-catalyzed preparation of (Z)-alkenes via β-hydride elimination, see: Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908 and references therein.
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For the Rh-catalyzed preparation of (Z)-alkenes via β-hydride elimination, see: Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908 and references therein.
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(b) Padwa, A.; Kassir, J. M.; Xu, S. E. J. Org. Chem. 1997, 62, 1642.
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For use of the Cu-catalysts shown in Table 1 in cyclopropenation and cyclopropanation, see: (a) Diaz-Requejo, M. M.; Mairena, M. A.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. Chem. Commun. 2001, 1804.
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For use of the Cu-catalysts shown in Table 1 in cyclopropenation and cyclopropanation, see: (a) Diaz-Requejo, M. M.; Mairena, M. A.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. Chem. Commun. 2001, 1804.
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For examples of Rh-catalyzed opening of cyclopropenes to putative akenylcarbene intermediates, see refs 3d and 8 and (a) Müller, P, Gränicher, C. Helv. Chim. Acta 1993, 76, 521
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For examples of Rh-catalyzed opening of cyclopropenes to putative akenylcarbene intermediates, see refs 3d and 8 and (a) Müller, P.; Gränicher, C. Helv. Chim. Acta 1993, 76, 521.
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For examples of azulene and hydroazulene synthesis via intramolecular variants of the Büchner synthesis, see (a) Chapter 6 in ref 1
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For examples of azulene and hydroazulene synthesis via intramolecular variants of the Büchner synthesis, see (a) Chapter 6 in ref 1.
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(b) Crombie, A. E.; Kane, J. L.; Shea, K. M.; Danheiser, R. E. J. Org. Chem. 2004, 69, 8652.
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In studies that compared C-H insertion to β-hydride elimination, Rh2-(Piv)4 was slightly more selective than Rh2(Piv)4. In one example, 12b 85:15 selectivity was observed with Rh2(Piv)4 versus 78:22 with Rh2-(OAc)4. See: (a) Taber, D. F.; Joshi, P. V. J. Org. Chem. 2004, 69, 4276.
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In studies that compared C-H insertion to β-hydride elimination, Rh2-(Piv)4 was slightly more selective than Rh2(Piv)4. In one example, 12b 85:15 selectivity was observed with Rh2(Piv)4 versus 78:22 with Rh2-(OAc)4. See: (a) Taber, D. F.; Joshi, P. V. J. Org. Chem. 2004, 69, 4276.
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(b) Taber, D. F.; Hennessy, M. J.; Louey, J. P. J. Org. Chem. 1992, 57, 436.
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J. Org. Chem
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Taber, D.F.1
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Louey, J.P.3
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34
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In a study that compared O-H insertion to β-hydride elimination in the reaction of α-diazohydrocinnamate with water, Rh2(OAc)4 gave 82:18 selectvily for O-H insertion, whereas Rh2(9-adamantoate)4 gave 88:12 selectivity: Cox, G. G, Haigh, D, Hindley, R. M, Miller, D. J, Moody, C. J. Tetrahedron Lett. 1994, 35, 3139
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In a study that compared O-H insertion to β-hydride elimination in the reaction of α-diazohydrocinnamate with water, Rh2(OAc)4 gave 82:18 selectvily for O-H insertion, whereas Rh2(9-adamantoate)4 gave 88:12 selectivity: Cox, G. G.; Haigh, D.; Hindley, R. M.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 3139.
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For mechanistic proposals for intermolecular cyclopropenation that involve the direct reaction of the alkyne with a tetrabridged Rh-carbenoid via a concerted, asynchronous transition state, see refs 6d and 6c and (a) Nowlan, D. T, III; Singleton, D. A. J. Am. Chem. Soc. 2005, 127, 6190
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For mechanistic proposals for intermolecular cyclopropenation that involve the direct reaction of the alkyne with a tetrabridged Rh-carbenoid via a concerted, asynchronous transition state, see refs 6d and 6c and (a) Nowlan, D. T., III; Singleton, D. A. J. Am. Chem. Soc. 2005, 127, 6190.
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For an alternate proposal in which ligand dissociation is thought to occur prior to cyclopropenation, see refs 6f and 6g. For mechanistic proposals in which ylide and alkenylcarbenes (analogous to 6 and 7) are considered as intermediates in intramolecular cyclopropenation, see ref 8b and (b) Padwa, A, Austin, D. J, Xu, S. E. Tetrahedron Lett. 1991, 32, 4103
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For an alternate proposal in which ligand dissociation is thought to occur prior to cyclopropenation, see refs 6f and 6g. For mechanistic proposals in which ylide and alkenylcarbenes (analogous to 6 and 7) are considered as intermediates in intramolecular cyclopropenation, see ref 8b and (b) Padwa, A.; Austin, D. J.; Xu, S. E. Tetrahedron Lett. 1991, 32, 4103.
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