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Volumn 42, Issue 33, 2003, Pages 3924-3927

Equilibrium and kinetic deuterium isotope effects on the hetero-Diels-Alder addition of sulfur dioxide

Author keywords

Ab initio calculations; Cycloaddition; Heterocycles; Isotope effects; Sulfur dioxide

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; DEUTERIUM; REACTION KINETICS;

EID: 0041317037     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351732     Document Type: Article
Times cited : (8)

References (29)
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    • For examples of kinetic deuterium isotope effects used to establish the synchronicity or asynchronicity of concerted Diels-Alder reactions: M. Taagepera, E. R. Thornton, J. Am. Chem. Soc. 1972, 94, 1168; J. J. Gajewski, K. B. Petersen, J. R. Kagel, Y. C. J. Huang, J. Am. Chem. Soc. 1989, 111, 9078; D.A. Singleton, S. R. Merrigan, B. R. Beno, K. N. Houk, Tetrahedron Lett. 1999, 40, 5817; D. A. Singleton, S. R. Merrigan, A. A. Thomas, Tetrahedron Lett. 1999, 40, 639; K. N. Houk, J. González, Y. Li, Acc. Chem. Res. 1995, 28, 81; N. Chronakis, M. Orfanopoulos, Org. Lett. 2001, 3, 545.
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    • For examples of kinetic deuterium isotope effects used to establish the synchronicity or asynchronicity of concerted Diels-Alder reactions: M. Taagepera, E. R. Thornton, J. Am. Chem. Soc. 1972, 94, 1168; J. J. Gajewski, K. B. Petersen, J. R. Kagel, Y. C. J. Huang, J. Am. Chem. Soc. 1989, 111, 9078; D.A. Singleton, S. R. Merrigan, B. R. Beno, K. N. Houk, Tetrahedron Lett. 1999, 40, 5817; D. A. Singleton, S. R. Merrigan, A. A. Thomas, Tetrahedron Lett. 1999, 40, 639; K. N. Houk, J. González, Y. Li, Acc. Chem. Res. 1995, 28, 81; N. Chronakis, M. Orfanopoulos, Org. Lett. 2001, 3, 545.
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    • For other studies on the hetero-Diels-Alder addition mechanisms, see e.g.: L. Kupczyk-Subotkowska, H. J. Shine, J. Am. Chem. Soc. 1993, 115, 5296; G. Orlova, J. D. Goddard, J. Org. Chem. 2001, 66, 4026; A. G. Leach, K. N. Houk, J. Org. Chem. 2001, 66, 5192; A. G. Leach, K. N. Houk, Chem. Commun. 2002, 1243.
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    • For other studies on the hetero-Diels-Alder addition mechanisms, see e.g.: L. Kupczyk-Subotkowska, H. J. Shine, J. Am. Chem. Soc. 1993, 115, 5296; G. Orlova, J. D. Goddard, J. Org. Chem. 2001, 66, 4026; A. G. Leach, K. N. Houk, J. Org. Chem. 2001, 66, 5192; A. G. Leach, K. N. Houk, Chem. Commun. 2002, 1243.
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    • Orlova, G.1    Goddard, J.D.2
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    • For other studies on the hetero-Diels-Alder addition mechanisms, see e.g.: L. Kupczyk-Subotkowska, H. J. Shine, J. Am. Chem. Soc. 1993, 115, 5296; G. Orlova, J. D. Goddard, J. Org. Chem. 2001, 66, 4026; A. G. Leach, K. N. Houk, J. Org. Chem. 2001, 66, 5192; A. G. Leach, K. N. Houk, Chem. Commun. 2002, 1243.
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    • Leach, A.G.1    Houk, K.N.2
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    • For other studies on the hetero-Diels-Alder addition mechanisms, see e.g.: L. Kupczyk-Subotkowska, H. J. Shine, J. Am. Chem. Soc. 1993, 115, 5296; G. Orlova, J. D. Goddard, J. Org. Chem. 2001, 66, 4026; A. G. Leach, K. N. Houk, J. Org. Chem. 2001, 66, 5192; A. G. Leach, K. N. Houk, Chem. Commun. 2002, 1243.
    • (2002) Chem. Commun. , pp. 1243
    • Leach, A.G.1    Houk, K.N.2


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