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For a nice review of strategies to access Z -alkenes, see: Siau, W.-Y.; Zhang, Y.; Zhao, Y. Top. Curr. Chem. 2012, 327, 33
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Koh, M. J.; Khan, R. K. M.; Torker, S.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2014, 53, 1968
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Gottumukkala, A. L.; Madduri, A. V. R.; Minnaard, A. J. ChemCatChem 2012, 4, 462
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Meek, S. J.; O'Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature 2011, 471, 461
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Meek, S.J.1
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Chen, C.; Dugan, T. R.; Brennessel, W. W.; Weix, D. J.; Holland, P. L. J. Am. Chem. Soc. 2014, 136, 945
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Chen, C.1
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Pünner, F.; Schmidt, A.; Hilt, G. Angew. Chem., Int. Ed. 2012, 51, 1270
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For access to Z -1,2-disubstituted allylamines a semi-hydrogenation approach is taken using propargylic N -phthalamides or ammonium salts using Lindlar's catalyst, which necessitates use of the alkyne and the added complications of using the phthalamide protecting group or running the reaction under acidic conditions; for an example, see
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For access to Z -1,2-disubstituted allylamines a semi-hydrogenation approach is taken using propargylic N -phthalamides or ammonium salts using Lindlar's catalyst, which necessitates use of the alkyne and the added complications of using the phthalamide protecting group or running the reaction under acidic conditions; for an example, see: Tomassy, B.; Zwierzak, A. Synth. Commun. 1998, 28, 1201
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Synth. Commun.
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Arenas, J. F.; Otero, J. C.; Peláez, D.; Soto, J. J. Chem. Phys. 2003, 119, 7814
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1842447549
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University Science Books: Sausalito, CA, pp xxxiii, 1084.
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Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Modern Molecular Photochemistry of Organic Molecules; University Science Books: Sausalito, CA, 2010; pp xxxiii, 1084.
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Turro, N.J.1
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Scaiano, J.C.3
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84865428662
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For an example of reductive quenching of the photocatalyst by an amine, see
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For an example of reductive quenching of the photocatalyst by an amine, see: Lalevee, J.; Tehfe, M.-A.; Dumur, F.; Gigmes, D.; Blanchard, N.; Morlet-Savary, F.; Fouassier, J. P. ACS Macro Lett. 2012, 1, 286
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Fouassier, J.P.7
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Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94
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Org. Lett.
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Condie, A.G.3
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Singh, A.; Arora, A.; Weaver, J. D. Org. Lett. 2013, 15, 5390
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Org. Lett.
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84864189655
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The barrier to isomerization of such an allylic radical is ∼15 kcal/mol; see
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The barrier to isomerization of such an allylic radical is ∼15 kcal/mol; see: Dibble, T. S.; Sha, Y.; Thornton, W. F.; Zhang, F. J. Phys. Chem. A 2012, 116, 7603
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J. Phys. Chem. A
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33646886959
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cis) approach unity for the isomerization of 1,3-dienes and stillbenes by high energy sensitizers; see: Hammond, G. S.; Saltiel, J.; Lamola, A. A.; Turro, N. J.; Bradshaw, J. S.; Cowan, D. O.; Counsell, R. C.; Vogt, V.; Dalton, C. J. Am. Chem. Soc. 1964, 86, 3197
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Hammond, G.S.1
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Turro, N.J.4
Bradshaw, J.S.5
Cowan, D.O.6
Counsell, R.C.7
Vogt, V.8
Dalton, C.9
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26
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84867095977
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3 has a peak emission at 520 nm in MeCN (55 kcal/mol)
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3 has a peak emission at 520 nm in MeCN (55 kcal/mol): Lu, Z.; Yoon, T. P. Angew. Chem., Int. Ed. 2012, 51, 10329
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Angew. Chem., Int. Ed.
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Lu, Z.1
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0000802962
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Houk found a barrier of only 1.2 kcal/mol for t Bu radical inversion, suggesting racemization would be fast if the radical was formed; see: Paddon-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 5046
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