A monomeric dilithio methandiide with a distorted trans-planar four-coordinate carbon

Angewandte Chemie - International Edition

Volumn 49, Issue 32, 2010, Pages 5570-5573

  Cooper, Oliver J ^a   Wooles, Ashley J ^a   McMaster, Jonathan ^a   Lewis, William ^a   Blake, Alexander J ^a   Liddle, Stephen T ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Lithium; Methandiide; N; P ligands; Planar four coordinate carbon; Structure elucidation

Indexed keywords

CARBON ATOMS; CARBON STRUCTURES; N; P LIGANDS; X-RAY DIFFRACTION STUDIES;

LIGANDS; X RAY DIFFRACTION;

LITHIUM;

EID: 77955037735     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002483     Document Type: Article

References (63)

1. Although le Bel is often jointly credited with van't Hoff for the proposal of tetrahedral four-coordinate carbon, it has been. pointed out that the credit should go to van't Hoff alone; see: a) N. N. Greenwood, J. Chem. Soc. Dalton Trans. 2001, 2055;
2. b) J. H. van't Hoff, Arch. Neerl. Sci. Exactes Nat. 1874, 445;
3. c) J. A. le Bel, Bull. Soc. Chim. Fr. 1874, 22, 337.
4. Selected references: a) M. Wu, Y. Pei, X. C. Zeng, J. Am. Chem. Soc. 2010, 132, 5554;
5. b) G. Merino, M. A. Méndez-Rojas, A. Vela, T. Heine, J. Comput. Chem. 2007, 28, 362;
6. c) P. D. Pancharatna, M. A. Méndez-Rojas, G. Merino, A. Vela, R. Hoffmann, J. Am. Chem. Soc. 2004, 126, 15309;
7. d) Z. X. Wang, P. von R. Schleyer, J. Am. Chem. Soc. 2002, 124, 11979;
8. e) R. Choukroun, P. Cassoux, Acc. Chem. Res. 1999, 32, 494;
9. f) W. Siebert, A. Gunale, Chem. Rev. 1999, 99, 367;
10. g) D. R. Rasmussen, L. Radom, Angew. Chem. 1999, 111, 3051;
11. Angew. Chem. Int. Ed. 1999, 38, 2875;
12. h) L. Radom, D. R. Rasmussen, Pure Appl. Chem. 1998, 70, 1977;
13. i) K. Sorger, P. von R. Schleyer, J. Mol. Struct. 1995, 338, 317.
14. R. Hoffmann, R. W. Alder, C. F. Wilcox, J. Am. Chem. Soc. 1970, 92, 4992.
15. -1; see: M. J. M. Pepper, I. Shavitt, P. von R. Schleyer, M. N. Glukhovtsev, R. Janoschek, M. Quack, J. Comput. Chem. 1995, 16, 207.
16. a) G. Erker, Chem. Soc. Rev. 1999, 28, 307;
17. b) D. Röttger, G. Erker, Angew. Chem. 1997, 109, 840;
18. Angew. Chem. Int. Ed. Engl. 1997, 36, 812,
19. and references therein. [6] J. B. Collins, J. D. Dill, E. D. Jemmis, Y. Apeloig, P. von R. Schleyer, R. Seeger, J. A. Pople, J. Am. Chem. Soc. 1976, 98, 5419.
20. K. Sorger, P. von R. Schleyer, R. Fleischer, D. Stalke, J. Am. Chem. Soc. 1996, 118, 6924.
21. A. Streitwieser, S. M. Bachrach, A. Dorigo, P. von R. Schleyer in Lithium Chemistry (Eds. : A. M. Sapse, P. von R. Schleyer), Wiley, New York, 1995, p. 19.
22. L. Orzechowski, G. Jansen, S. Harder, Angew. Chem. 2009, 121, 3883;
23. Angew. Chem. Int. Ed. 2009, 48, 3825.
24. G. D. Stucky, M. M. Eddy, W. H. Harrison, R. Lagow, H. Kawa, D. E. Cox, J. Am. Chem. Soc. 1990, 112, 2425.
25. a) J. H. Chen, J. Guo, Y. Li, C. W. So, Organometallics 2009, 28, 4617;
26. b) G. Linti, A. Rodig, H. Pritzkow, Angew. Chem. 2002, 114, 4685;
27. Angew. Chem. Int. Ed. 2002, 41, 4503;
28. c) J. F. K. Müller, M. Neuburger, B. Spingier, Angew. Chem. 1999, 111, 97;
29. Angew. Chem. Int. Ed. 1999, 38, 92;
30. d) W. Zarges, M. Marsch, K. Harms, G. Boche, Chem. Ber. 1989, 122, 1307.
31. A. Kasani, R. P. Kamalesh Babu, R. McDonald, R. G. Cavell, Angew. Chem. 1999, 111, 1580;
32. Angew. Chem. Int. Ed. 1999, 38, 1483.
33. C. M. Ong, D. W. Stephan, J. Am. Chem. Soc. 1999, 121, 2939.
34. a) K. L. Hull, I. Carmichael, B. C. Noll, K. W. Henderson, Chem. Eur. J. 2008, 14, 3939;
35. b) K. L. Hull, B. C. Noll, K. W. Henderson, Organometallics 2006, 25, 4072.
36. O. J. Cooper, J. McMaster, W. Lewis, A. J. Blake, S. T. Liddle, Dalton Trans. 2010, 39, 5074.
37. a) M. Demange, L. Boubekeur, A. Auffrant, N. Mézailles, L. Ricard, X. Le Goff, P. Le Floch, New J. Chem. 2006, 30, 1745;
38. b) T. Cantat, L. Ricard, P. Le Floch, N. Mézailles, Organometallics 2006, 25, 4965.
39. a) A. J. Wooles, O. J. Cooper, J. McMaster, W. Lewis, A. J. Blake, S. T. Liddle, Organometallics 2010, 29, 2315;
40. b) A. J. Wooles, D. P. Mills, W. Lewis, A. J. Blake, S. T. Liddle, Dalton Trans. 2010, 39, 500;
41. c) D. P. Mills, A. J. Wooles, J. McMaster, W. Lewis, A. J. Blake, S. T. Liddle, Organometallics 2009, 28, 6771;
42. d) D. P. Mills, O. J. Cooper, J. McMaster, W. Lewis, S. T. Liddle, Dalton Trans. 2009, 4547;
43. e) S. T. Liddle, D. P. Mills, B. M. Gardner, J. McMaster, C. Jones, W. Woodul, Inorg. Chem. 2009, 48, 3520;
44. f) S.T. Liddle, J. McMaster, J. Green, P. L. Arnold, Chem. Commun. 2008, 1747.
45. S. Al-Benna, M. J. Sarsfield, M. Thornton-Pett, D. L. Ormsby, P. J. Maddox, P. Brès, M. Bochmann, J. Chem. Soc. Dalton Trans. 2000, 4247.
46. -3. CCDC 774584 (2) and 774585 (3) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
47. www.ccdc.cam.ac.uk/data-request/cif.
48. The absence of Li-C contacts in substituted methanides is not uncommon; see: S. T. Liddle, D. P. Mills, A. J. Wooles, Organomet. Chem. 2010, 36, 29, and references therein.
49. a) K. Gregory, P. von R. Schleyer, R. Snaith, Adv. Inorg. Chem. 1991, 37, 47;
50. b) R. E. Mulvey, Chem. Soc. Rev. 1991, 20, 167.
51. See the Supporting Information for full details.
52. Tmeda has long been known to activate organolithium reagents; see: B. J. Wakefield in The Chemistry of Organolithium Compounds, Pergamon, Elmsford, New York, 1974.
53. Closely related carbodiphosphoranes exhibit a range of P-C-P angles, indicating a shallow potential energy surface with respect to bending; see: a) G. E. Hardy, W. C. Kaska, B. P. Chandra, J. I. Zink, J. Am. Chem. Soc. 1981, 103, 1074;
54. b) G. E. Hardy, J. I. Zink, W. C. Kaska, J. C. Baldwin, J. Am. Chem. Soc. 1978, 100, 8001;
55. c) A. T. Vincent, P. J. Wheatley, J. Chem. Soc. Dalton Trans. 1972, 617.
56. P. Pyykkö, M. Atsumi, Chem. Eur. J. 2009, 15, 186.
57. S. S. Batsanov, Inorg. Mater. 2001, 37, 871.
58. a) C. Fonseca Guerra, J. G. Snijders, G. te Velde, E. J. Baerends, Theor. Chem. Acc. 1998, 99, 391;
59. b) G. te Velde, F. M. Bickelhaupt, S. J. A. van Gisbergen, C. Fonseca Guerra, E. J. Baerends, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931.
60. E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, Weinhold, F. NBO 5.0., Theoretical Chemistry Institute, University of Wisconsin: Madison, 2001.
61. C. Lambert, P. von R. Schleyer, Angew. Chem. 1994, 106, 1187;
62. Angew. Chem. Int. Ed. Engl. 1994, 33, 1129.
63. As discussed in Ref. [17c], a 'captodative' description of the bonding in 3 is also worthy of consideration; see: M. Alcarazo, C. W. Lehmann, A. Anoop, W. Thiel, A. Fürstner, Nat. Chem. 2009, 1, 295.