A crystallographic map of chiral recognition in π complexes of aromatic aldehydes and a chiral transition metal Lewis acid: Enantioface binding selectivities in solution correlate to distances Between metal and carbon stereocenters in the solid state

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2411-2421

  Boone, Brian J ^a   Klein, Darryl P ^a   Seyler, Jeffery W ^a   Méndez, N Quirós ^a   Arif, A M ^a   Gladysz, J A ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; RHENIUM;

ARTICLE; COMPLEX FORMATION; DRUG BINDING; STEREOCHEMISTRY;

EID: 0029939813     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953523t     Document Type: Article

References (100)

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2. Lead references to an extensive literature: (a) Peacock, S. C.; Domeier, L. A.; Gaeta, F. C. A.; Helgeson, R. C.: Timko, J. M.; Cram. D. J. J. Am. Chem. Soc. 1978, 100, 8190. (b) Peacock, S. S.: Walba, D. M.; Gaeta, F. C. A.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1980, 102, 2043. (c) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511. (d) Andelman, D.; Orland. H. J. Am. Chem. Soc. 1993, 115, 12322. (e) Owens. L.; Thilgen, C.; Diederich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757, and references therein, (f) Burger, M. T.; Armstrong, A.: Guarnieri. F.; McDonald, D. Q.: Still, W. C. J. Am. Chem. Soc. 1994, 116, 3593. (g) Mizutani, T.; Ema, T.: Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 4240. (h) Sawada, M.: Takai, Y.; Yamada, H.: Hirayama, S.; Kaneda, T.: Tanaka, T.: Kamada, K.: Mizooku. T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe. Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726.
3. Lead references to an extensive literature: (a) Peacock, S. C.; Domeier, L. A.; Gaeta, F. C. A.; Helgeson, R. C.: Timko, J. M.; Cram. D. J. J. Am. Chem. Soc. 1978, 100, 8190. (b) Peacock, S. S.: Walba, D. M.; Gaeta, F. C. A.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1980, 102, 2043. (c) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511. (d) Andelman, D.; Orland. H. J. Am. Chem. Soc. 1993, 115, 12322. (e) Owens. L.; Thilgen, C.; Diederich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757, and references therein, (f) Burger, M. T.; Armstrong, A.: Guarnieri. F.; McDonald, D. Q.: Still, W. C. J. Am. Chem. Soc. 1994, 116, 3593. (g) Mizutani, T.; Ema, T.: Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 4240. (h) Sawada, M.: Takai, Y.; Yamada, H.: Hirayama, S.; Kaneda, T.: Tanaka, T.: Kamada, K.: Mizooku. T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe. Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726.
4. Lead references to an extensive literature: (a) Peacock, S. C.; Domeier, L. A.; Gaeta, F. C. A.; Helgeson, R. C.: Timko, J. M.; Cram. D. J. J. Am. Chem. Soc. 1978, 100, 8190. (b) Peacock, S. S.: Walba, D. M.; Gaeta, F. C. A.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1980, 102, 2043. (c) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511. (d) Andelman, D.; Orland. H. J. Am. Chem. Soc. 1993, 115, 12322. (e) Owens. L.; Thilgen, C.; Diederich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757, and references therein, (f) Burger, M. T.; Armstrong, A.: Guarnieri. F.; McDonald, D. Q.: Still, W. C. J. Am. Chem. Soc. 1994, 116, 3593. (g) Mizutani, T.; Ema, T.: Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 4240. (h) Sawada, M.: Takai, Y.; Yamada, H.: Hirayama, S.; Kaneda, T.: Tanaka, T.: Kamada, K.: Mizooku. T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe. Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726.
5. Lead references to an extensive literature: (a) Peacock, S. C.; Domeier, L. A.; Gaeta, F. C. A.; Helgeson, R. C.: Timko, J. M.; Cram. D. J. J. Am. Chem. Soc. 1978, 100, 8190. (b) Peacock, S. S.: Walba, D. M.; Gaeta, F. C. A.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1980, 102, 2043. (c) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511. (d) Andelman, D.; Orland. H. J. Am. Chem. Soc. 1993, 115, 12322. (e) Owens. L.; Thilgen, C.; Diederich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757, and references therein, (f) Burger, M. T.; Armstrong, A.: Guarnieri. F.; McDonald, D. Q.: Still, W. C. J. Am. Chem. Soc. 1994, 116, 3593. (g) Mizutani, T.; Ema, T.: Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 4240. (h) Sawada, M.: Takai, Y.; Yamada, H.: Hirayama, S.; Kaneda, T.: Tanaka, T.: Kamada, K.: Mizooku. T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe. Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726.
6. Lead references to an extensive literature: (a) Peacock, S. C.; Domeier, L. A.; Gaeta, F. C. A.; Helgeson, R. C.: Timko, J. M.; Cram. D. J. J. Am. Chem. Soc. 1978, 100, 8190. (b) Peacock, S. S.: Walba, D. M.; Gaeta, F. C. A.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1980, 102, 2043. (c) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511. (d) Andelman, D.; Orland. H. J. Am. Chem. Soc. 1993, 115, 12322. (e) Owens. L.; Thilgen, C.; Diederich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757, and references therein, (f) Burger, M. T.; Armstrong, A.: Guarnieri. F.; McDonald, D. Q.: Still, W. C. J. Am. Chem. Soc. 1994, 116, 3593. (g) Mizutani, T.; Ema, T.: Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 4240. (h) Sawada, M.: Takai, Y.; Yamada, H.: Hirayama, S.; Kaneda, T.: Tanaka, T.: Kamada, K.: Mizooku. T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe. Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726.
7. Lead references to an extensive literature: (a) Peacock, S. C.; Domeier, L. A.; Gaeta, F. C. A.; Helgeson, R. C.: Timko, J. M.; Cram. D. J. J. Am. Chem. Soc. 1978, 100, 8190. (b) Peacock, S. S.: Walba, D. M.; Gaeta, F. C. A.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1980, 102, 2043. (c) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511. (d) Andelman, D.; Orland. H. J. Am. Chem. Soc. 1993, 115, 12322. (e) Owens. L.; Thilgen, C.; Diederich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757, and references therein, (f) Burger, M. T.; Armstrong, A.: Guarnieri. F.; McDonald, D. Q.: Still, W. C. J. Am. Chem. Soc. 1994, 116, 3593. (g) Mizutani, T.; Ema, T.: Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 4240. (h) Sawada, M.: Takai, Y.; Yamada, H.: Hirayama, S.; Kaneda, T.: Tanaka, T.: Kamada, K.: Mizooku. T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe. Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726.
8. Lead references to an extensive literature: (a) Peacock, S. C.; Domeier, L. A.; Gaeta, F. C. A.; Helgeson, R. C.: Timko, J. M.; Cram. D. J. J. Am. Chem. Soc. 1978, 100, 8190. (b) Peacock, S. S.: Walba, D. M.; Gaeta, F. C. A.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1980, 102, 2043. (c) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511. (d) Andelman, D.; Orland. H. J. Am. Chem. Soc. 1993, 115, 12322. (e) Owens. L.; Thilgen, C.; Diederich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757, and references therein, (f) Burger, M. T.; Armstrong, A.: Guarnieri. F.; McDonald, D. Q.: Still, W. C. J. Am. Chem. Soc. 1994, 116, 3593. (g) Mizutani, T.; Ema, T.: Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 4240. (h) Sawada, M.: Takai, Y.; Yamada, H.: Hirayama, S.; Kaneda, T.: Tanaka, T.: Kamada, K.: Mizooku. T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe. Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726.
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18. See also Halterman, R. L.; McEvoy, M. A. J. Am. Chem. Soc. 1992, 114, 980.
19. Aliphatic aldehyde complexes of I: (a) Garner, C. M.; Quiros Méndez. N.; Kowalczyk, J. J.: Fernández, J. M.: Emerson, K.; Larsen, R. D.; Gladysz, J. A. J. Am. Chem. Soc. 1990, 112, 5146. (b) Dalton, D. M.; Garner, C. M.; Fernández, J. M.; Gladysz, J. A. J. Org. Chem. 1991, 56, 6823. (c) Klein, D. P.; Quirós Méndez, N.; Seyler, J. W.; Arif, A. M.; Gladysz, J. A. J. Organomet. Chem. 1993, 450, 157.
20. Aliphatic aldehyde complexes of I: (a) Garner, C. M.; Quiros Méndez. N.; Kowalczyk, J. J.: Fernández, J. M.: Emerson, K.; Larsen, R. D.; Gladysz, J. A. J. Am. Chem. Soc. 1990, 112, 5146. (b) Dalton, D. M.; Garner, C. M.; Fernández, J. M.; Gladysz, J. A. J. Org. Chem. 1991, 56, 6823. (c) Klein, D. P.; Quirós Méndez, N.; Seyler, J. W.; Arif, A. M.; Gladysz, J. A. J. Organomet. Chem. 1993, 450, 157.
21. Aliphatic aldehyde complexes of I: (a) Garner, C. M.; Quiros Méndez. N.; Kowalczyk, J. J.: Fernández, J. M.: Emerson, K.; Larsen, R. D.; Gladysz, J. A. J. Am. Chem. Soc. 1990, 112, 5146. (b) Dalton, D. M.; Garner, C. M.; Fernández, J. M.; Gladysz, J. A. J. Org. Chem. 1991, 56, 6823. (c) Klein, D. P.; Quirós Méndez, N.; Seyler, J. W.; Arif, A. M.; Gladysz, J. A. J. Organomet. Chem. 1993, 450, 157.
22. Aromatic aldehyde complexes of I: (a) Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 1473. (b) Quirós Méndez, N.; Mayne, C. L.; Gladysz, J. A. Angew, Chem., Int. Ed. Engl. 1990, 29, 1475. (c) Klein. D. P.: Gladysz, J. A. J. Am. Chem. Soc. 1992, 144, 8710. (d) Quiros Méndez, N.; Seyler, J. W.: Arif, A. M.: Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 2323. (e) Boone, B. J.; Klein, D. P.; Quiros Méndez, N.: Seyler. J. W.; Arif, A. M.; Gladysz. J. A. J. Chem. Soc., Chem. Commun. 1995, 279.
23. Aromatic aldehyde complexes of I: (a) Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 1473. (b) Quirós Méndez, N.; Mayne, C. L.; Gladysz, J. A. Angew, Chem., Int. Ed. Engl. 1990, 29, 1475. (c) Klein. D. P.: Gladysz, J. A. J. Am. Chem. Soc. 1992, 144, 8710. (d) Quiros Méndez, N.; Seyler, J. W.: Arif, A. M.: Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 2323. (e) Boone, B. J.; Klein, D. P.; Quiros Méndez, N.: Seyler. J. W.; Arif, A. M.; Gladysz. J. A. J. Chem. Soc., Chem. Commun. 1995, 279.
24. Aromatic aldehyde complexes of I: (a) Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 1473. (b) Quirós Méndez, N.; Mayne, C. L.; Gladysz, J. A. Angew, Chem., Int. Ed. Engl. 1990, 29, 1475. (c) Klein. D. P.: Gladysz, J. A. J. Am. Chem. Soc. 1992, 144, 8710. (d) Quiros Méndez, N.; Seyler, J. W.: Arif, A. M.: Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 2323. (e) Boone, B. J.; Klein, D. P.; Quiros Méndez, N.: Seyler. J. W.; Arif, A. M.; Gladysz. J. A. J. Chem. Soc., Chem. Commun. 1995, 279.
25. Aromatic aldehyde complexes of I: (a) Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 1473. (b) Quirós Méndez, N.; Mayne, C. L.; Gladysz, J. A. Angew, Chem., Int. Ed. Engl. 1990, 29, 1475. (c) Klein. D. P.: Gladysz, J. A. J. Am. Chem. Soc. 1992, 144, 8710. (d) Quiros Méndez, N.; Seyler, J. W.: Arif, A. M.: Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 2323. (e) Boone, B. J.; Klein, D. P.; Quiros Méndez, N.: Seyler. J. W.; Arif, A. M.; Gladysz. J. A. J. Chem. Soc., Chem. Commun. 1995, 279.
26. Aromatic aldehyde complexes of I: (a) Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 1473. (b) Quirós Méndez, N.; Mayne, C. L.; Gladysz, J. A. Angew, Chem., Int. Ed. Engl. 1990, 29, 1475. (c) Klein. D. P.: Gladysz, J. A. J. Am. Chem. Soc. 1992, 144, 8710. (d) Quiros Méndez, N.; Seyler, J. W.: Arif, A. M.: Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 2323. (e) Boone, B. J.; Klein, D. P.; Quiros Méndez, N.: Seyler. J. W.; Arif, A. M.; Gladysz. J. A. J. Chem. Soc., Chem. Commun. 1995, 279.
27. Monosubstituted alkene complexes of I: (a) Bodner, G. S.: Peng, T.-S.; Arif, A. M.: Gladysz, J. A. Organometallics 1990, 9, 1191. (b) Peng, T.-S.: Arif. A. M.; Gladysz, J. A. Helv. Chim. Acta 1992, 75, 442. (c) Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174. (d) Pene, T.-S.; Gladysz, J. A. Organometallics 1995, 14, 898. (e) Wang. Y.; Gladysz, J. A. Chem. Ber. 1995, 128, 213. (f) Peng, T.-S.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1995, 1857. (g) Sanau, M.: Peng. T.-S.: Arif. A. M.: Gladysz, J. A. J. Organomet. Chem. 1995, 503, 235.
28. Monosubstituted alkene complexes of I: (a) Bodner, G. S.: Peng, T.-S.; Arif, A. M.: Gladysz, J. A. Organometallics 1990, 9, 1191. (b) Peng, T.-S.: Arif. A. M.; Gladysz, J. A. Helv. Chim. Acta 1992, 75, 442. (c) Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174. (d) Pene, T.-S.; Gladysz, J. A. Organometallics 1995, 14, 898. (e) Wang. Y.; Gladysz, J. A. Chem. Ber. 1995, 128, 213. (f) Peng, T.-S.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1995, 1857. (g) Sanau, M.: Peng. T.-S.: Arif. A. M.: Gladysz, J. A. J. Organomet. Chem. 1995, 503, 235.
29. Monosubstituted alkene complexes of I: (a) Bodner, G. S.: Peng, T.-S.; Arif, A. M.: Gladysz, J. A. Organometallics 1990, 9, 1191. (b) Peng, T.-S.: Arif. A. M.; Gladysz, J. A. Helv. Chim. Acta 1992, 75, 442. (c) Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174. (d) Pene, T.-S.; Gladysz, J. A. Organometallics 1995, 14, 898. (e) Wang. Y.; Gladysz, J. A. Chem. Ber. 1995, 128, 213. (f) Peng, T.-S.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1995, 1857. (g) Sanau, M.: Peng. T.-S.: Arif. A. M.: Gladysz, J. A. J. Organomet. Chem. 1995, 503, 235.
30. Monosubstituted alkene complexes of I: (a) Bodner, G. S.: Peng, T.-S.; Arif, A. M.: Gladysz, J. A. Organometallics 1990, 9, 1191. (b) Peng, T.-S.: Arif. A. M.; Gladysz, J. A. Helv. Chim. Acta 1992, 75, 442. (c) Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174. (d) Pene, T.-S.; Gladysz, J. A. Organometallics 1995, 14, 898. (e) Wang. Y.; Gladysz, J. A. Chem. Ber. 1995, 128, 213. (f) Peng, T.-S.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1995, 1857. (g) Sanau, M.: Peng. T.-S.: Arif. A. M.: Gladysz, J. A. J. Organomet. Chem. 1995, 503, 235.
31. Monosubstituted alkene complexes of I: (a) Bodner, G. S.: Peng, T.-S.; Arif, A. M.: Gladysz, J. A. Organometallics 1990, 9, 1191. (b) Peng, T.-S.: Arif. A. M.; Gladysz, J. A. Helv. Chim. Acta 1992, 75, 442. (c) Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174. (d) Pene, T.-S.; Gladysz, J. A. Organometallics 1995, 14, 898. (e) Wang. Y.; Gladysz, J. A. Chem. Ber. 1995, 128, 213. (f) Peng, T.-S.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1995, 1857. (g) Sanau, M.: Peng. T.-S.: Arif. A. M.: Gladysz, J. A. J. Organomet. Chem. 1995, 503, 235.
32. Monosubstituted alkene complexes of I: (a) Bodner, G. S.: Peng, T.-S.; Arif, A. M.: Gladysz, J. A. Organometallics 1990, 9, 1191. (b) Peng, T.-S.: Arif. A. M.; Gladysz, J. A. Helv. Chim. Acta 1992, 75, 442. (c) Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174. (d) Pene, T.-S.; Gladysz, J. A. Organometallics 1995, 14, 898. (e) Wang. Y.; Gladysz, J. A. Chem. Ber. 1995, 128, 213. (f) Peng, T.-S.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1995, 1857. (g) Sanau, M.: Peng. T.-S.: Arif. A. M.: Gladysz, J. A. J. Organomet. Chem. 1995, 503, 235.
33. Monosubstituted alkene complexes of I: (a) Bodner, G. S.: Peng, T.-S.; Arif, A. M.: Gladysz, J. A. Organometallics 1990, 9, 1191. (b) Peng, T.-S.: Arif. A. M.; Gladysz, J. A. Helv. Chim. Acta 1992, 75, 442. (c) Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174. (d) Pene, T.-S.; Gladysz, J. A. Organometallics 1995, 14, 898. (e) Wang. Y.; Gladysz, J. A. Chem. Ber. 1995, 128, 213. (f) Peng, T.-S.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1995, 1857. (g) Sanau, M.: Peng. T.-S.: Arif. A. M.: Gladysz, J. A. J. Organomet. Chem. 1995, 503, 235.
34. 1,3-Enone, enal, diene, and glyoxal complexes of I: (a) Wang, Y.; Agbossou, F.; Dalton. D. M.; Liu, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2699. (b) Peng, T.-S.; Wang, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 4535. (c) Wang, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 2164.
35. 1,3-Enone, enal, diene, and glyoxal complexes of I: (a) Wang, Y.; Agbossou, F.; Dalton. D. M.; Liu, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2699. (b) Peng, T.-S.; Wang, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 4535. (c) Wang, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 2164.
36. 1,3-Enone, enal, diene, and glyoxal complexes of I: (a) Wang, Y.; Agbossou, F.; Dalton. D. M.; Liu, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2699. (b) Peng, T.-S.; Wang, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 4535. (c) Wang, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 2164.
37. Other alkene complexes of I: (a) Kowalczyk, I. J.: Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729. (b) Pu, J.: Peng. T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Peng, T.-S.; Pu. J.; Gladysz, J. A. Organometallics 1994, 13, 929.
38. Other alkene complexes of I: (a) Kowalczyk, I. J.: Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729. (b) Pu, J.: Peng. T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Peng, T.-S.; Pu. J.; Gladysz, J. A. Organometallics 1994, 13, 929.
39. Other alkene complexes of I: (a) Kowalczyk, I. J.: Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729. (b) Pu, J.: Peng. T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Peng, T.-S.; Pu. J.; Gladysz, J. A. Organometallics 1994, 13, 929.
40. Analogous pentamethylcyclopentadienyl aldehyde and alkene complexes: (a) Agbossou, F.; Ramsden, J. A.; Huang, Y.-H.; Arif, A. M.; Gladysz, J. A. Organometallics 1992, 11, 693. (b) Peng, T.-S.; Winter, C. H.: Gladysz, J. A. Inorg. Chem. 1994, 33, 2534.
41. Analogous pentamethylcyclopentadienyl aldehyde and alkene complexes: (a) Agbossou, F.; Ramsden, J. A.; Huang, Y.-H.; Arif, A. M.; Gladysz, J. A. Organometallics 1992, 11, 693. (b) Peng, T.-S.; Winter, C. H.: Gladysz, J. A. Inorg. Chem. 1994, 33, 2534.
42. (a) Schilling, B. E. R.: Hoffmann, R.; Faller, J. W. J. Am. Chem. Soc. 1979. 101, 592.
43. (b) Czech, P. T.; Gladysz, J. A.; Fenske, R. F. Organometallics 1989, 8, 1806.
44. 6a,10b Carbon configurations are omitted for mixtures of enantiomerically pure π/π′ isomers. (b) All isomer ratios are normalized to 100.
45. 3 ligand do not.
46. - would not necessarily be equal in π and π′ isomers. However, they should undergo parallel changes as aryl substituents are varied.
47. Boone, B. J.; Quirós Méndez, N.; Mayne, C. L.; Gladysz, J. A. manuscript in preparation.
48. - has not been reported previously. It was prepared and characterized similarly to the other complexes (Experimental Section).
49. 13C resonances (π/π′. 75 MHz: 75.2/74.8. 76.0/75.8 ppm; baseline resolved at 125 MHz).
50. x calculations utilized equation 6.5c, as opposed to 6.7a.
51. 2 varies from 1.325 g/mL at 293 K to 1.508 g/mL at 193 K: Industrial Solvents Handbook, 4th ed.; Flick, E. W., Ed.; Noyes Data Corp: Park Ridge, NJ. 1991.
52. 2 varies only slightly over these intervals, concentration effects play only minor roles in temperature dependences.
53. For a discussion of error limits on integrals in nonreplicated NMR spectra, see: Derome. A. E. Modern NMR Techniques for Chemistry Research: Pergamon: New York, 1987: Chapter 7.6.
54. Siegel, J. S.; Anet. F. A. L. J. Org. Chem. 1988, 53, 2629.
55. - (0.13 M) -/90:10 (263 K), 90:10/89:11 (243 K), 90:10/89:11 (223 K), 91:9/91:9 (203 K). 92:8/90:10 (183 K).
56. - yielded data of extremely poor quality due either to severe disorder or the presence of more than one independent molecule in the unit cell.
57. (a) Eisenstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1981, 103, 4308.
58. (b) Cameron, A. D.; Smith, V. H. Jr.; Baird, M. C. J. Chem. Soc., Dalton Trans. 1988, 1037.
59. 2C=CHAr bond lengths vary irregularly (2.174(13)/1.374(18), 2.180(12)/1.454(17), 2.137-(17)/1.419(25) Å). Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1976, 1865.
60. The slippage value is 0% when the perpendicular from rhenium to the O=C bond intercepts the midpoint, as in an equilateral triangle. At the other limit, the slippage value is 100% when the perpendicular intersects the oxygen or carbon atom.
61. 5) (O=C 1.333(12) and 1.376 (9) Å): (a) Brunner, H.; Wachter, J.: Bernai, I.: Creswick, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 861. (b) Creswick, M. W.; Bernal, I. Inorg. Chim. Acta 1983, 71, 41. (c) Rabinovich, D.; Parkin, G. J. Am. Chem. Soc. 1991, 113, 5904.
62. 5) (O=C 1.333(12) and 1.376 (9) Å): (a) Brunner, H.; Wachter, J.: Bernai, I.: Creswick, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 861. (b) Creswick, M. W.; Bernal, I. Inorg. Chim. Acta 1983, 71, 41. (c) Rabinovich, D.; Parkin, G. J. Am. Chem. Soc. 1991, 113, 5904.
63. 5) (O=C 1.333(12) and 1.376 (9) Å): (a) Brunner, H.; Wachter, J.: Bernai, I.: Creswick, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 861. (b) Creswick, M. W.; Bernal, I. Inorg. Chim. Acta 1983, 71, 41. (c) Rabinovich, D.; Parkin, G. J. Am. Chem. Soc. 1991, 113, 5904.
64. (a) Brown, J. M.; Mertis, K. J. Organomet. Chem. 1973, 47, C5.
65. (b) Gust, D.: Mislow. K. J. Am. Chem. Soc. 1973, 95, 2854.
66. (c) Faller, J. W.; Johnson, B. V. J. Organomet. Chem. 1975, 96, 99.
67. (d) Bye. E.; Schweizer, B.; Dunitz, J. D. J. Am. Chem. Soc. 1982, 104, 5893.
68. (e) Brunner. H.: Hammer, B.; Krüger, C.; Angermund, K.: Bernal, I. Organometallics 1985, 4, 1063.
69. (f) Davies, S. G.; Derome, A. E.; McNally, J. P. J. Am. Chem. Soc. 1991, 113, 2854.
70. (g) Polowin, J.; Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724.
71. (h) Garner, S. E.: Orpen, A. G. J. Chem. Soc., Dalton Trans. 1993, 533.
72. (i) Brunner, H.; Oeschey, R.; Nuber, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 866.
73. This generalization also includes π formaldehyde, thioformaldehyde, selenoformaldehyde, and 1,3-difluoroacetone adducts of I: (a) Buhro, W. E.: Georgiou, S.: Fernández, J. M.; Patton, A. T.: Strouse, C. E.: Gladysz, J. A. Organometallics 1986, 5, 956. (b) Buhro, W. E.: Etter, M. C.; Georgiou, S.; Gladysz. J. A.: McCormick. F. B. Organometallics 1987, 6, 1150. (c) McCormick, F. B. Organometallics 1984, 3, 1924. (d) Klein, D. P.: Dalton, D. M.; Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. J. Organomet. Chem. 1991, 412, C7.
74. This generalization also includes π formaldehyde, thioformaldehyde, selenoformaldehyde, and 1,3-difluoroacetone adducts of I: (a) Buhro, W. E.: Georgiou, S.: Fernández, J. M.; Patton, A. T.: Strouse, C. E.: Gladysz, J. A. Organometallics 1986, 5, 956. (b) Buhro, W. E.: Etter, M. C.; Georgiou, S.; Gladysz. J. A.: McCormick. F. B. Organometallics 1987, 6, 1150. (c) McCormick, F. B. Organometallics 1984, 3, 1924. (d) Klein, D. P.: Dalton, D. M.; Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. J. Organomet. Chem. 1991, 412, C7.
75. This generalization also includes π formaldehyde, thioformaldehyde, selenoformaldehyde, and 1,3-difluoroacetone adducts of I: (a) Buhro, W. E.: Georgiou, S.: Fernández, J. M.; Patton, A. T.: Strouse, C. E.: Gladysz, J. A. Organometallics 1986, 5, 956. (b) Buhro, W. E.: Etter, M. C.; Georgiou, S.; Gladysz. J. A.: McCormick. F. B. Organometallics 1987, 6, 1150. (c) McCormick, F. B. Organometallics 1984, 3, 1924. (d) Klein, D. P.: Dalton, D. M.; Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. J. Organomet. Chem. 1991, 412, C7.
76. This generalization also includes π formaldehyde, thioformaldehyde, selenoformaldehyde, and 1,3-difluoroacetone adducts of I: (a) Buhro, W. E.: Georgiou, S.: Fernández, J. M.; Patton, A. T.: Strouse, C. E.: Gladysz, J. A. Organometallics 1986, 5, 956. (b) Buhro, W. E.: Etter, M. C.; Georgiou, S.; Gladysz. J. A.: McCormick. F. B. Organometallics 1987, 6, 1150. (c) McCormick, F. B. Organometallics 1984, 3, 1924. (d) Klein, D. P.: Dalton, D. M.; Quirós Méndez, N.; Arif, A. M.: Gladysz, J. A. J. Organomet. Chem. 1991, 412, C7.
77. 31c,d
78. -. However, analogous trends are well established for other types of carbonyl compounds: Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.: Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644.
79. (b) Rosenberg, R. E. Jr. J. Am. Chem. Soc. 1995, 117, 10358.
80. (c) Curtis, M. D.; Shiu, K.-B.; Butler, W. M. J. Am. Chem. Soc. 1986, 108, 1550.
81. (d) Durfee, L. D.; Rothwell, I. P. Chem. Rev. 1988, 88, 1059.
82. -1.
83. Barlow, R. Statistics: Wiley: New York, 1989; Chapter 8.3.1.
84. - salts.
85. (a) Brunner, H. Angew, Chem., Int. Ed. Engl. 1983, 22, 897: see sections 6-8.
86. (b) Nishio, M.: Umezawa, Y.: Hirota, M.; Takeuchi, Y. Tetrahedron 1995. 51, 8665.
87. 8a,b,g,9b are longer than those in the aldehyde complexes (Charts 2 and 3).
88. Distances between fluorine atoms of the anions and non-hydrogen atoms of the cations are all greater than 3.0 Å. Analogous distances to hydrogen atoms of the cations are greater than 2.3 Å.
89. - with some Lewis acids.
90. (a) Giovannetti, J. S.; Kelly, C. M.; Landis. C. R. J. Am. Chem. Soc. 1993. 115, 4040.
91. (b) Bender, B. R.; Koller. M.: Nanz, D.: von Philipsborn, W. J. Am. Chem. Soc. 1993, 115, 5889.
92. (c) Burk, M. J.: Feaster, J. E.; Nugent. W. A.; Harlow. R. L. J. Am. Chem. Soc. 1993, 115, 10125.
93. Jablonski, C. R. Aldrich. Acta 1990, 23, 58.
94. NO value were identical with those of the corresponding tetrafluoroborate salt.
95. Agbossou, F.; O'Connor, E. J.; Garner, C. M.: Quirós Méndez, N.; Fernández. J. M.; Patton. A. T.; Ramsden, J. A.; Gladysz, J. A. Inorg. Synth. 1992, 29, 211.
96. -.
97. (a) Buhro, W. E.; Zwick, B. D.; Georgiou, S.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 2427.
98. (b) Zwick, B. D.; Dewey, M. A.; Knight, D. A.; Buhro, W. E.; Arif, A. M.: Gladysz, J. A. Organometallics 1992, 11, 2673.
99. Frenz, B. A. In The Enraf-Nonius CAD 4 SDP - A Real-time System for Concurrent X-ray Data Collection and Crystal Structure Determination. In Computing and Crystallography; Schenk, H., Olthof-Hazelkamp, R., van Konigsveld, H., Bassi, G. C., Eds.; Delft University Press: Delft, Holland, 1978; pp 64-71.
100. Cromer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch: Birmingham, England, 1974; Volume IV, pp 72-98, 149-150; tables 2.2B and 2.3.1.