Chelation-based stabilization of the transition structure in a lithium diisopropylamide mediated dehydrobromination: Avoiding the 'universal ground state' assumption

Journal of the American Chemical Society

Volumn 119, Issue 24, 1997, Pages 5573-5582

  Remenar, Julius F ^a   Collum, David B ^a  

^a Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CHELATE; LITHIUM; LITHIUM DERIVATIVE; LITHIUM DIISOPROPYLAMIDE; NITROGEN 15; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHELATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLVATION; TEMPERATURE DEPENDENCE;

EID: 0030810795     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970030a     Document Type: Article

References (132)

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37. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
38. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
39. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
40. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
41. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
42. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
43. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
44. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
45. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
46. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
47. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
48. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
49. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
50. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
51. (a) For an example of autocatalysis of an N-alkylation by LiBr, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524. (b) For leading references to apparent lithium amide mixed aggregation effects, see: Hall, P.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198. (c) For additional lithium amide mixed aggregation effects, see: Seebach, D. Synthesis 1993, 1271. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Nichols, M. A.; Waldmuller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153. Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1. Bunn, B. J.; Simpkins, N. S.; Spavold, Z.; Crimmin, M. J. J. Chem. Soc., Perkin Trans. 1 1993, 3113. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, E. J. Am. Chem. Soc. 1996, 118, 6924. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. Mair, F. S.; Clegg, W.; Oneil, P. A. J. Am. Chem. Soc. 1993, 115, 3388. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Sugasawa, K.; Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377.
52. Elimination of 0.1 M 1 by 0.1 M LDA (1.0 equiv) in THF shows no sign of autocatalysis despite the buildup of substantial concentrations of LiBr.
53. 23,41
54. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1989, 111, 6772.
55. n affords n = 1.02 ± 0.15.
56. 2THF begin to appear.
57. 18
58. Endo, K.; Otsu, T. Macromol. Rapid Commun. 1994, 15, 233. Poshyachinda, S.; Edwards, H. G. M.; Johnson, A. F. Polymer 1991, 32, 338. Bywater, S.; Black, P.; Worsfold, D. J.; Schue, F. Macromolecules 1985, 18, 335. Fraenkel, G.; Geckle, M. J.; Kaylo, A.; Estes, D. W. J. Organomet. Chem. 1980, 197, 249. Sugahara, K.; Fujita, T.; Watanabe, S.; Hashimoto, H. J. Chem. Technol. Biotechnol. 1987, 37, 95. Fujita, T.; Watanabe, S.; Suga, K.; Sugahara, K.; Tsuchimoto, K. Chem. Ind. 1983, 167.
59. Endo, K.; Otsu, T. Macromol. Rapid Commun. 1994, 15, 233. Poshyachinda, S.; Edwards, H. G. M.; Johnson, A. F. Polymer 1991, 32, 338. Bywater, S.; Black, P.; Worsfold, D. J.; Schue, F. Macromolecules 1985, 18, 335. Fraenkel, G.; Geckle, M. J.; Kaylo, A.; Estes, D. W. J. Organomet. Chem. 1980, 197, 249. Sugahara, K.; Fujita, T.; Watanabe, S.; Hashimoto, H. J. Chem. Technol. Biotechnol. 1987, 37, 95. Fujita, T.; Watanabe, S.; Suga, K.; Sugahara, K.; Tsuchimoto, K. Chem. Ind. 1983, 167.
60. Endo, K.; Otsu, T. Macromol. Rapid Commun. 1994, 15, 233. Poshyachinda, S.; Edwards, H. G. M.; Johnson, A. F. Polymer 1991, 32, 338. Bywater, S.; Black, P.; Worsfold, D. J.; Schue, F. Macromolecules 1985, 18, 335. Fraenkel, G.; Geckle, M. J.; Kaylo, A.; Estes, D. W. J. Organomet. Chem. 1980, 197, 249. Sugahara, K.; Fujita, T.; Watanabe, S.; Hashimoto, H. J. Chem. Technol. Biotechnol. 1987, 37, 95. Fujita, T.; Watanabe, S.; Suga, K.; Sugahara, K.; Tsuchimoto, K. Chem. Ind. 1983, 167.
61. Endo, K.; Otsu, T. Macromol. Rapid Commun. 1994, 15, 233. Poshyachinda, S.; Edwards, H. G. M.; Johnson, A. F. Polymer 1991, 32, 338. Bywater, S.; Black, P.; Worsfold, D. J.; Schue, F. Macromolecules 1985, 18, 335. Fraenkel, G.; Geckle, M. J.; Kaylo, A.; Estes, D. W. J. Organomet. Chem. 1980, 197, 249. Sugahara, K.; Fujita, T.; Watanabe, S.; Hashimoto, H. J. Chem. Technol. Biotechnol. 1987, 37, 95. Fujita, T.; Watanabe, S.; Suga, K.; Sugahara, K.; Tsuchimoto, K. Chem. Ind. 1983, 167.
62. Endo, K.; Otsu, T. Macromol. Rapid Commun. 1994, 15, 233. Poshyachinda, S.; Edwards, H. G. M.; Johnson, A. F. Polymer 1991, 32, 338. Bywater, S.; Black, P.; Worsfold, D. J.; Schue, F. Macromolecules 1985, 18, 335. Fraenkel, G.; Geckle, M. J.; Kaylo, A.; Estes, D. W. J. Organomet. Chem. 1980, 197, 249. Sugahara, K.; Fujita, T.; Watanabe, S.; Hashimoto, H. J. Chem. Technol. Biotechnol. 1987, 37, 95. Fujita, T.; Watanabe, S.; Suga, K.; Sugahara, K.; Tsuchimoto, K. Chem. Ind. 1983, 167.
63. Endo, K.; Otsu, T. Macromol. Rapid Commun. 1994, 15, 233. Poshyachinda, S.; Edwards, H. G. M.; Johnson, A. F. Polymer 1991, 32, 338. Bywater, S.; Black, P.; Worsfold, D. J.; Schue, F. Macromolecules 1985, 18, 335. Fraenkel, G.; Geckle, M. J.; Kaylo, A.; Estes, D. W. J. Organomet. Chem. 1980, 197, 249. Sugahara, K.; Fujita, T.; Watanabe, S.; Hashimoto, H. J. Chem. Technol. Biotechnol. 1987, 37, 95. Fujita, T.; Watanabe, S.; Suga, K.; Sugahara, K.; Tsuchimoto, K. Chem. Ind. 1983, 167.
64. Lucht, B. L.; Collum, D. J. Am. Chem. Soc. 1996, 118, 10707.
65. 2a However, several simplifying algebraic assumptions, while not seriously flawed, seem less appropriate in hindsight.
66. (a) If solvation is non-cooperative, then the ground and transition state corresponding to the mixed solvated LDA will correspond to the mean value of the homosolvated ground states and transition states (respectively) in Figure 4.
67. (b) Benson, S. W. J. Am. Chem. Soc. 1958, 80, 5151.
68. 2].
69. Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 9863.
70. A, Table 1) has been adjusted to account for the statistical bias imparted by two equivalent methoxy groups.
71. 4/n-BuOMe) = 1.02 ± 0.10.
72. Lyons, B. A.; Pfeifer, J.; Peterson, T.; Carpenter, B. K. J. Am. Chem. Soc. 1993, 115, 2427.
73. 1. For related studies see ref 8.
74. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Williard, P. G. Unpublished.
75. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Williard, P. G. Unpublished.
76. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166.
77. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
78. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
79. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
80. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
81. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
82. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
83. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
84. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
85. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
86. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J.
87. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
88. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
89. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
90. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
91. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
92. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
93. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
94. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
95. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
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97. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
98. Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 44, 2865. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valu, G. S. J. Org. Chem. 1993, 58, 750. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328. Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 2166. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008. Bernstein, M. P. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1993. Koch, R.; Wiedel, Anders, E. J. Org. Chem. 1996, 61, 2523. Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165. Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955. Harder, S.; van Lenthe, J. H.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1994, 116, 2508. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. Shimano, M.; Meyers, A. I. J. Org. Chem. 1996, 61, 5714. Alvaro, G.; Savoia, D.; Valentini, M. R. Tetrahedron 1996, 38, 12571. Williard, P. G. Unpublished.
99. 27
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102. For leading references to theoretical investigations of dehydrohalogenations, see: Glad, S. S.; Jensen, F. J. Org. Chem. 1997, 62, 253. Gronert, S. J. Org. Chem. 1994, 59, 7046. Dewar, M. J. S.; Yuan, Y.-C. J. Am. Chem. Soc. 1990, 112, 2088.
103. For leading references to theoretical investigations of dehydrohalogenations, see: Glad, S. S.; Jensen, F. J. Org. Chem. 1997, 62, 253. Gronert, S. J. Org. Chem. 1994, 59, 7046. Dewar, M. J. S.; Yuan, Y.-C. J. Am. Chem. Soc. 1990, 112, 2088.
104. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
105. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
106. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
107. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
108. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
109. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
110. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
111. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
112. There are a number of reports where ostensibly weaker solvent-lithium interactions lead to increased overall reaction rates: Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1541. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Bywater, S.; Worsfold, D. J. Can. J. Chem. 1962, 40, 1564. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc. 1989, 111, 1804. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543. Reich, H. J.; Dykstra, R. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1469. See refs 2a, 3, and 18.
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