Diphenylphosphidoboratabenzene: An anionic analogue of triphenylphosphine

Journal of the American Chemical Society

Volumn 118, Issue 34, 1996, Pages 8176-8177

  Hoic, Diego A ^a   Davis, William M ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG STRUCTURE;

EID: 0029788478     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9615740     Document Type: Article

References (21)

1. For a review of phosphine complexes of transition metals, see: Dias, P. B.; de Piedade, M. E. M,; Simoes, J. A. M. Coord. Chem. Rev. 1994, 135, 737-807.
2. Qiao, S.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc: 1996, 118, 6329-6330.
3. This general approach has proved to be extremely interesting in early transition metal metallocene chemistry. For examples and leading references, see: (a) Crowther, D. J.; Baenziger, N. C.; Jordan, R. F. J. Am. Chem. Soc. 1991, 113, 1455-1457.
4. (b) Quan, R. W.; Bazan, G. C; Kiely, A. F.: Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4489-4490.
5. 2 = 0.1104 (for data with 1 > 2σ(I)); GOF = 1.411. All computations were handled by the Siemens software package (SMART, SAINT, SHELXTL).
6. Kreutzer, K. A.; Fisher, R. A.; Davis, W. M.; Spaltenstein, E.; Buchwald, S. L. Organometallics 1991, 10, 4031-4035.
7. 2 = 0.1389 for data with I > 2σ(I); GOF = 1.290.
8. For a discussion, see: Brunner, H.; Hammer, B.; Kruger, C; Angermund, K.; Bernai, I. Organometallics 1985, 4, 1063-1068.
9. 2O: Riley, P. E.; Davis, R. E. Organametallics 1983, 2, 286-292. See also: Davison, A.; Green, M. L. H.; Wilkinson, G. J. Chem. Soc. 1961, 3172-3177.
10. 2O: Riley, P. E.; Davis, R. E. Organametallics 1983, 2, 286-292. See also: Davison, A.; Green, M. L. H.; Wilkinson, G. J. Chem. Soc. 1961, 3172-3177.
11. 2]-: Sim, G. A.: Woodhouse, D. I.; Knox, G. R. J. Chem. Soc., Dalton Trans. 1979, 629-635.
12. 6 differ by less than 0.01 Å for all of the bond distances reported in Table 2.
13. 2): Burckett-St. Laurent, J. C. T. R.; Haines, R. J.; Nolte, C. R.; Steen, N. D. C. T. Inorg. Chem. 1980, 19, 577-587.
14. 2 = 0.1000 for data with I > 2σ(I); GOF = 1.166.
15. For a closely related structure, see: Thorn, D. L.; Harlow, R. L. Inorg. Chem. 1990, 29, 2017-2019.
16. 2 results in the formation of two rhodium hydride species. Further investigations are underway.
17. DPB adducts 3-5 are the first boratabenzene complexes in which the ligand is σ-bound, rather than π-bound, to the metal. For leading references to π-bound boratabenzene complexes, see: (a) Herberich, G. E. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 1, Chapter 5. (b) Herberich, G. E.; Ohst, H. Adv. Organomet. Chem. 1986, 25, 199-236. (C) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Muller, C. J. Am. Chem. Soc: 1996, 118, 2291-2292.
18. DPB adducts 3-5 are the first boratabenzene complexes in which the ligand is σ-bound, rather than π-bound, to the metal. For leading references to π-bound boratabenzene complexes, see: (a) Herberich, G. E. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 1, Chapter 5. (b) Herberich, G. E.; Ohst, H. Adv. Organomet. Chem. 1986, 25, 199-236. (C) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Muller, C. J. Am. Chem. Soc: 1996, 118, 2291-2292.
19. DPB adducts 3-5 are the first boratabenzene complexes in which the ligand is σ-bound, rather than π-bound, to the metal. For leading references to π-bound boratabenzene complexes, see: (a) Herberich, G. E. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 1, Chapter 5. (b) Herberich, G. E.; Ohst, H. Adv. Organomet. Chem. 1986, 25, 199-236. (C) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Muller, C. J. Am. Chem. Soc: 1996, 118, 2291-2292.
20. 3Cl with potassium diphenylamidoboratabenzene.
21. 1 ligands in which the ligating atom is both stereogenic and configurationally stable are rare. See: Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis; VCH: New York, 1993; Vol. 2.