Hemilabile Ligands in Organolithium Chemistry: Substituent Effects on Lithium Ion Chelation

Journal of the American Chemical Society

Volumn 125, Issue 50, 2003, Pages 15376-15387

  Ramírez, Antonio ^a   Lobkovsky, Emil ^a   Collum, David B ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RATE LAWS;

CHELATION; COMPUTATIONAL METHODS; LITHIUM; LITHIUM COMPOUNDS; MONOMERS; POLYETHERS;

ORGANOMETALLICS;

1 BROMOCYCLOOCTENE; AMINOETHER; CYCLOOCTYNE; ETHER DERIVATIVE; LIGAND; LITHIUM DIISOPROPYLAMIDE; LITHIUM ION; MONOMER; ORGANOLITHIUM COMPOUND; POLYETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELIMINATION REACTION; ORGANIC CHEMISTRY; REACTION ANALYSIS; SOLVATION;

CHELATING AGENTS; CRYSTALLOGRAPHY, X-RAY; CYCLOOCTANES; ETHANOLAMINE; ETHERS, CYCLIC; KINETICS; LIGANDS; LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; THERMODYNAMICS;

EID: 0346218217     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030322d     Document Type: Article

References (213)

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23. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
24. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
25. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
26. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
27. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
28. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
29. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
30. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
31. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
32. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
33. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
34. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
35. For leading references to base-mediated eliminations of vinyl halides, see: Jacobs, T. L. Org. React. 1949, 5, 1. Bohlmann, F. Angew. Chem. 1957, 69, 82. Franke, G.; Ziengenbein, W.; Meister, H. Angew. Chem. 1960, 72, 391. Arens, J. F. In Advances in Organic Chemistry; Interscience Publishers: New York. 1960; Vol 2, p 121. Kobrich, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 49. Kobrich, G.; Buck, P. In Chemistry of Acetylenes; Viche, H. G., Ed.; Marcel Dekker: New York, 1969; p 99. Brandsma, L. In Preparative Acetylenic Chemistry; Elsevier: Amsterdam. 1971. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, 1978; p 635. Ben-Efraim, D. A. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 755. Demlow, E. V.; Lisse, M. Liebigs Ann. Chem. 1980, 1. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1988. Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Ed.; VCH: Weinheim, 1995; p 285. Furber, M. In Comprehensive Organic Functional Group Transformations: Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, p 1062.
36. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
37. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
38. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
39. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
40. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
41. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
42. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
43. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
44. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
45. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
46. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
47. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
48. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
49. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Hammond, G. S. Steric Effects in Organic Chemistry, Newman, M. S. Ed., Wiley: New York, 1956. Eliel, E. Stereochemistry of Carbon Compounds; McGraw-Hill Book Comp.: New York, 1962: p 197. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. I, p 43. See also: Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. Jung, M. E. Synlett 1999, 843. Parrill, A. L.; Dolata, D. P. J. Mol. Struct. (THEOCHEM) 1996, 370, 182. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789. Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319. Keese, R.; Meyer, M. Tetrahedron 1993, 49, 2055. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Schleyer, P. v. R. J. Am. Chem. Soc. 1961, 83, 1368. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
50. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
51. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
52. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
53. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
54. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
55. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
56. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
57. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
58. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
59. The gem-dimethyl effect and affiliated Thorpe-Ingold effect10 have been discussed in the context of organometallic chemistry: Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031. Casey, C. P. ; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096. Barkley, J.; Ellis, M.; Higgins, S. J.; McCart, M. K. Organometallics 1998, 17, 1725. Desper, J. M.; Gellman, S. H.; Wolf, R. E., Jr.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5278. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307. Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Newman, M. S.; Busch, D. H.; Cheney, G. E.; Gustafson, C. R. Inorg. Chem. 1972, 12, 2890.
60. Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080. Ingold, C. K. J. Chem. Soc. 1921, 119, 305.
61. Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080. Ingold, C. K. J. Chem. Soc. 1921, 119, 305.
62. Also, see the rigid group principle: Schmiegel, J.; Funke, U.; Mix, A.; Gruetzmacher, H. F. Chem. Ber. 1990, 123, 1397. Voegtle, F.; Mayenfels, P.; Luppertz, F. Synthesis 1984, 580. Rasshofer, W.; Oepen, G.; Mueller, W. M.; Voegtle, F. Chem. Ber. 1978, 111, 1108. Siemeing, U. Polyhedron 1997, 16, 1513.
63. Also, see the rigid group principle: Schmiegel, J.; Funke, U.; Mix, A.; Gruetzmacher, H. F. Chem. Ber. 1990, 123, 1397. Voegtle, F.; Mayenfels, P.; Luppertz, F. Synthesis 1984, 580. Rasshofer, W.; Oepen, G.; Mueller, W. M.; Voegtle, F. Chem. Ber. 1978, 111, 1108. Siemeing, U. Polyhedron 1997, 16, 1513.
64. Also, see the rigid group principle: Schmiegel, J.; Funke, U.; Mix, A.; Gruetzmacher, H. F. Chem. Ber. 1990, 123, 1397. Voegtle, F.; Mayenfels, P.; Luppertz, F. Synthesis 1984, 580. Rasshofer, W.; Oepen, G.; Mueller, W. M.; Voegtle, F. Chem. Ber. 1978, 111, 1108. Siemeing, U. Polyhedron 1997, 16, 1513.
65. Also, see the rigid group principle: Schmiegel, J.; Funke, U.; Mix, A.; Gruetzmacher, H. F. Chem. Ber. 1990, 123, 1397. Voegtle, F.; Mayenfels, P.; Luppertz, F. Synthesis 1984, 580. Rasshofer, W.; Oepen, G.; Mueller, W. M.; Voegtle, F. Chem. Ber. 1978, 111, 1108. Siemeing, U. Polyhedron 1997, 16, 1513.
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105. 15N]LDA solvated ligands H-R are archived in Supporting Information.
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110. The concentration of the lithium amide, although expressed in units of molarity, refers to the concentration of the monomer unit (normality).
111. Espenson, J. H. Chemical Kinetics and Reaction Mechanisms; McGraw-Hill: New York, 1995; p 15.
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115. The failure of the crown ethers (OO-QQ, Chart 3) to promote rate accelerations that exceed those of simple diethers (CC and JJ) is consistent with structural studies showing crowns are not particularly strong ligands for lithium amide monomers.21b
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127. MNDO calculations exaggerate steric effects: Scano, P.; Thomson, C. J. Comput. Chem. 1991, 12, 172. Stewart, J. J. P. J. Comput.-Aided Mol. Des. 1990, 4, 1. Also, see ref 28a.
128. 2NLi fragments were removed without modification of the chelating ligand. The strain energies of the resulting ligand conformers were obtained by a single-point calculation. Although this did not appear to offer compelling insights in this particular case, we have archived the results in Supporting Information.
129. (b) Hay, B. P.; Rustad, J. R.; Hostetler, C. J. J. Am. Chem. Soc. 1993, 11, 5, 11158. Hay, B. P.; Rustad, J. R. J. Am. Chem. Soc. 1994, 116, 6316.
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132. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Gill, A.; Nanayakkara, C.; Gonzalez, M.; Challacombe, P. M. W.; Johnson, B.; Chen, W. ; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
133. The Ahlrichs all-electron SVP basis set was used for Br, and 6-31G* was used for the rest. This basis set is denoted as 631A and has been previously applied to mechanistic studies on organolithium-mediated reactions: Nakamura, E.; Yamanaka, M.; Yoshikai, N.; Mori, S. Angew. Chem., Int. Ed. 2001, 40, 1935. Mori, J.; Nakamura, E.; Morokuma, K. J. Am. Chem. Soc. 2000, 122, 7294 and references therein.
134. The Ahlrichs all-electron SVP basis set was used for Br, and 6-31G* was used for the rest. This basis set is denoted as 631A and has been previously applied to mechanistic studies on organolithium-mediated reactions: Nakamura, E.; Yamanaka, M.; Yoshikai, N.; Mori, S. Angew. Chem., Int. Ed. 2001, 40, 1935. Mori, J.; Nakamura, E.; Morokuma, K. J. Am. Chem. Soc. 2000, 122, 7294 and references therein.
135. Narula, A. S. Tetrahedron Lett. 1981, 27, 4119.
136. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
137. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
138. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
139. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
140. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
141. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
142. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
143. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
144. Considerable evidence points to a continuum of mechanisms in the range E2-Elcb for the elimination of HX from halo-substituted alkenes: Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195. Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1988, 110, 7136. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374. Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. Gassman, P. G.; Valcho, J. J. J. Am. Chem. Soc. 1975, 97, 4768. Modena, G.; Marchese, G.; Naso, F.; Tangari, N. J. Chem. Soc. B 1970, 1196. Kwok, W. K.; Lee, W. G.; Miller, S. I. J. Am. Chem. Soc. 1969, 91, 468. Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. B 1968, 958. Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
145. Haffner, F.; Sun, C.; Williard, P. G. J. Am. Chem. Soc. 2000, 122, 12542.
146. For examples of trigonal bipyramidal pentacoordinated lithium amide monomers, see: Poctschke, N.; Nieger, M.; Khan, M. A.; Niecke, E.; Ashby, M. T. Inorg. Chem. 1997, 36, 4087. Kremer, T.; Hampel, F.; Knoch, F. A.; Bauer, W.; Schmidt, A.; Gabold, P.; Schtz, M.; Ellermann, J.; Schleyer, P. v. R. Organometallics 1996, 15, 4776.
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151. Yakimansky, A. V.; Müller, A. H. E. J. Am. Chem. Soc. 2001, 123, 4932. Badiali, J.-P.; Cachet, H.; Cyrot, A.; Lestrade, J.-C. J. Chem. Soc., Faraday Trans. 1973, 1339. Cachet, H.; Cyrot, A.; Fekir, M.; Lestrade, J.-C. J. Phys. Chem. 1979, 83, 2419. Ashby, E. C.; Dobbs, F. R.; Hopkins, H. P., Jr. J. Am. Chem. Soc. 1973, 95, 2823. Matsuda, Y.; Morita, M.; Tachihara, F. Bull. Chem. Soc. Jpn. 1986, 59, 1967. Delsignore, M.; Maaser, H. E.; Petrucci, S. J. Phys. Chem. 1984, 88, 2405. Tobishima, S.; Yamaji, A. Electrochim. Acta 1983, 28, 1067. See also refs 38a, c-e.
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153. Yakimansky, A. V.; Müller, A. H. E. J. Am. Chem. Soc. 2001, 123, 4932. Badiali, J.-P.; Cachet, H.; Cyrot, A.; Lestrade, J.-C. J. Chem. Soc., Faraday Trans. 1973, 1339. Cachet, H.; Cyrot, A.; Fekir, M.; Lestrade, J.-C. J. Phys. Chem. 1979, 83, 2419. Ashby, E. C.; Dobbs, F. R.; Hopkins, H. P., Jr. J. Am. Chem. Soc. 1973, 95, 2823. Matsuda, Y.; Morita, M.; Tachihara, F. Bull. Chem. Soc. Jpn. 1986, 59, 1967. Delsignore, M.; Maaser, H. E.; Petrucci, S. J. Phys. Chem. 1984, 88, 2405. Tobishima, S.; Yamaji, A. Electrochim. Acta 1983, 28, 1067. See also refs 38a, c-e.
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155. Evidence of high-coordinate lithium amides: (a) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 9863.
156. (b) Lucht, B. L.; Bernstein, M. P.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 10707.
157. (c) Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524.
158. (d) Henderson, K. W.; Dorigo, A. E.; Liu, Q.-Y.; Williard, P. G. J. Am. Chem. Soc. 1997, 119, 11855.
159. (e) See ref 37.
160. The key structural data for the crystal structures 23 and 24 are located in Supporting Information and have been archived in the Cambridge Crystallographic Database (23, CCDC 208621; 24, CCDC 208620).
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