[Lithium tert-butylperoxide]12: Crystal structure of an aggregated oxenoid

Chemistry - A European Journal

Volumn 2, Issue 5, 1996, Pages 604-607

  Boche, Gernot ^a   Möbus, Konrad ^a   Harms, Klaus ^a   Lohrenz, John C W ^a   Marsch, Michael ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Aggregates; Lithium compounds; Oxenoids; Peroxides; Structure elucidation

Indexed keywords

OTHER PROPERTIES; OXENOIDS; OXIDATION REACTIONS; QUANTUM-CHEMICAL CALCULATION; STRUCTURE ELUCIDATION; THEORETICAL STUDY; TRANSITION STATE; X RAY CRYSTAL STRUCTURES;

LITHIUM; LITHIUM COMPOUNDS; ORGANOMETALLICS; OXIDATION; OXYGEN; PEROXIDES; QUANTUM CHEMISTRY;

AGGREGATES;

EID: 0000439467     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020521     Document Type: Article

References (57)

1. a) F. Di Furia, G. Modena, Pure Appl. Chem. 1982, 54, 1853-1866;
2. b) S. Campestrini, V. Conte, F. Di Furia, G. Modena, D. Bortolini, J. Org. Chem. 1988, 53, 5721-5724.
3. a) S. S. Woodard, M. G. Finn, K. B. Sharpless, J. Am. Chem. Soc. 1991, 113, 106-113;
4. b) M. G. Finn, K. B. Sharpless, J. Am. Chem. Soc. 1991, 113, 113-126, and references cited therein.
5. a) S.-H. Zhao, O. Samuel, H. B. Kagan, Tetrahedron 1987, 43, 5135-5144, and references cited therein;
6. b) H. B. Kagan in Stereochemistry of Organic and Bioorganic Transformations (Eds.: W. Bartmann, K. B. Sharpless), VCH, Weinheim, 1987, pp. 31-48.
7. W. R. Thiel, T. Priermeier, Angew. Chem. 1995, 107, 1870-1871;
8. Angew. Chem. Int. Ed. Engl. 1995, 34, 1737-1738.
9. K. Machii, Y. Watanabe, I. Morishima, J. Am. Chem. Soc. 1995, 117, 6691-6697.
10. J. Kim, E. Larka, E. C. Wilkinson, L. Que, Jr., Angew. Chem. 1995, 107, 2191-2194;
11. Angew. Chem. Int. Ed. Engl. 1995, 34, 2048-2051.
12. M. Lubben, A. Meetsma, E. C. Wilkinson, B. Feringa, L. Que, Jr., Angew. Chem. 1995, 107, 1610-1612;
13. Angew. Chem. Int. Ed. Engl. 1995, 34, 1512-1514.
14. (η5-C5Me5)2Hf(C2H5)(OOtBu) and its transformation into (η5-C5Me5)2́Hf(C2H5O)(OtBu): A. van Asselt, B. D. Santarsiero, J. E. Bercaw, J. Am. Chem. Soc. 1986, 108, 8291-8293.
15. Cambridge Structural Database, update October 1994.
16. H. Mimoun, P. Chaumette, M. Mignard, L. Saussine, J. Fischer, R. Weiss, Nouv. J. Chim. 1983, 7, 467-475;
17. G. Boche, K. Möbus, K. Harms, M. Marsch, J. Am. Chem. Soc. 1996, 118, in press.
18. a) G. Boche, F. Bosold, J. C. W. Lohrenz, Angew. Chem. 1994, 106, 1228-1230;
19. Angew. Chem. Int. Ed. Engl. 1994, 33, 1161-1163, and references cited therein; see also
20. b) M. Julia, N. P. Saint-Jalmes, J.-N. Verpeaux, Synlett. 1993, 233-234;
21. M. Julia, V. Pfeuty-Saint Jaimes, K. Plé, J.-N. Verpeaux, G. Hollingworth, Bull. Soc. Chim. Fr. 1996, 133, 15-24.
22. J. F. McGarrity, C. A. Ogle, Z. Brich, H.-R. Loosli, J. Am. Chem. Soc. 1985, 107, 1810-1815.
23. a) H. Abbotto, A. Streitwieser, Jr., J. Am. Chem. Soc. 1995, 117, 6358-6359;
24. b) H. Luitjes, M. Schakel, R. F. Schmitz, G. W. Klumpp, Angew. Chem. 1995, 107, 2324-2315;
25. Angew. Chem. Int. Ed. Engl. 1995, 34, 2152-2153.
26. The mean value of the O-O bond length in 18 molecules of the type MOOR [M = metal(complex)] amounts to 146.7 pm (ref. [9]).
27. a) G. Sosnovsky, J. H. Brown, Chem. Rev. 1966, 66, 529-566;
28. b) M. Maher-Detweiler, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, vol. E13, 1988, part 1, pp. 176-213;
29. c) U. Schöllkopf, ibid. vol. 13/1, 1970, pp. 170-253;
30. d) K. Nützel, ibid. vol. 13/2a, 1973, pp. 234-251;
31. e) K.-F. Wedemeyer, ibid. vol. 6/1c, 1976, part 1, pp. 141-146;
32. f) K. Geibel, H. Hofmann, H. Kropf, J. Thiem, ibid. vol. 6/1a, 1979, part 1, pp. 217-224;
33. g) K. Nützel, ibid. vol. 13/2a, 1973, pp. 700-706;
34. h) K. Nützel, ibid. vol. 13/2a, 1973, pp. 908-915.
35. P. Warner, S.-L. Lu, J. Org. Chem. 1976, 41, 1459-1461.
36. E. J. Panek, L. R. Kaiser, G. M. Whitesides, J. Am. Chem. Soc. 1977, 99, 3708-3713.
37. G. Boche, M. Möller, unpublished results.
38. G. Boche, M. Husemann, unpublished results.
39. a) R. D. Bach, G. J. Wolber, B. A. Coddens, J. Am. Chem. Soc. 1984, 106, 6098-6099;
40. b) R. D. Bach, M.-D. Su, J. L. Andrés, H. B. Schlegel, ibid. 1993, 115, 8763-8769;
41. c) K. A. Jørgensen, J. Chem. Soc. Perkin Trans. 2 1994, 117-124;
42. d) Ref. [11a]; see also
43. e) K. A. Jørgensen, R. A. Wheeler, R. Hoffmann, J. Am. Chem. Soc. 1987, 109, 3240-3246;
44. f) Y.-D. Wu, D. K. W. Lai, J. Org. Chem. 1995, 60, 673-680.
45. a) G. Boche, F. Bosold, J. C. W. Lohrenz, A. Opel, P. Zulauf, Chem. Ber. 1993, 126, 1873-1885;
46. b) G. Boche, A. Opel, M. Marsch, K. Harms, F. Haller, J. C. W. Lohrenz, C. Thümmler, W. Koch, ibid. 1992, 125, 2265-2273;
47. c) G. Boche, J. C. W. Lohrenz, A. Opel in Lithium Chemistry: A Theoretical and Experimental Overview (Eds.: P. v. R. Schleyer, A.-M. Sapse), J. Wiley, New York, 1995, pp. 195-225.
48. G. Boche, C. Boie, F. Bosold, K. Harms, M. Marsch, Angew. Chem. 1994, 106, 90-91;
49. Angew. Chem. Int. Ed. Engl. 1994, 33, 115-117.
50. 2-LiOOH (4): 4-31/G(d) 147.2 pm; 6-31/G(d) 146.2 pm; CISD/6-31 G(d) 146.2 pm [20c]; MP2/6-31G(d) 151.8 pm [20b].
51. +] 150.3 pm. Thus, the O-O bond lengths in these aggregates are similarly shorter than in the monomer 4 (151.8 pm); however, the shortening is less pronounced than in the HF/6-31 + G(d)5D calculations.
52. 2 is observed in the case of a monomeric and a dimeric carbenoid 9 and nitrenoid 10 on the C-O and N-O bonds, respectively (G. Boche and J. C. W. Lohrenz, unpublished results).
53. Siemens SHELXTL-PLUS (VMS) Version 4.21, Siemens Analytical X-Ray Instruments, Madison, 1990.
54. G. M. Sheldrick, SHELXL-93, Program for the Refinement of Crystal Structures, Göttingen 1993.
55. A. L. Spek, Platon 92, Program for Geometrical Analysis of Crystal Structures, Utrecht, 1992.
56. E. Keller, SCHAKAL-88B, A FORTRAN Program for the Graphic Representation of Molecular and Crystallographic Models, Freiburg, 1988.
57. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC-1220-3. Copies of the data can be obtained free of charge on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: Int. code+(1223)336-033; e-mail: teched@chemcrys.cam.ac.uk).