Tetrahedrane - Dossier of an unknown

Chemistry - A European Journal

Volumn 12, Issue 28, 2006, Pages 7411-7420

  Nemirowski, Adelina ^a   Reisenauer, Hans Peter ^a   Schreiner, Peter R ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

Carbenes; Spherical aromaticity; Strained molecules; Tetrahedrane

Indexed keywords

AROMATIC COMPOUNDS; COMPUTER SIMULATION; ELECTRONIC PROPERTIES; GROUND STATE; REACTION KINETICS; THERMODYNAMICS;

CARBENES; SPHERICAL AROMATICITY; STRAINED MOLECULES; TETRAHEDRANE;

MOLECULAR STRUCTURE;

EID: 33749242238     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600451     Document Type: Article

References (84)

1. a) G. Maier, S. Pfriem, U. Schaefer, R. Matusch, Angew. Chem. 1978, 90, 552-553;
2. Angew. Chem. Int. Ed. Engl. 1978, 17, 520-521;
3. b)G. Maier, F. Fleischer, Tetrahedron Lett. 1991, 32, 57-59;
4. c) G. Maier, S. Pfriem, U. Schaefer, K. D. Maisch, R. Matusch, Chem. Ber. 1981, 114, 3965-3987;
5. d) G. Maier, D. Born, Angew. Chem. 1989, 707, 1085-1087;
6. Angew. Chem. Int. Ed. Engl. 1989, 28, 1050-1052;
7. e) G. Maier, R. Wolf, H.-O. Kalinowski, Angew. Chem. 1992, 704, 764-766;
8. Angew. Chem. Im. Ed. Engl. 1992, 31, 738-740;
9. f) G. Maier, R. Wolf, H.-O. Kalinowski, Chem. Ber. 1994, 727, 201-204;
10. g) G. Maier, F. Fleischer, H.-O. Kalinowski, Liebigs Ann. 1995, 173-186;
11. h) G. Maier, J. Neudert, O. Wolf, Angew. Chem. 2001, 775, 1719-1720;
12. Angew. Chem. Int. Ed. 2001, 40, 1674-1675;
13. i) A. Sekiguchi, M. Tanaka, J. Am. Chem. Soc. 2003, 725, 12684-12685;
14. j) M. Tanaka, A. Sekiguchi, Angew. Chem. 2005, 117, 5971-5973;
15. Angew. Chem. Int. Ed. 2005, 44, 5821-5823.
16. A. Baeyer, Chem. Ber. 1885, 18, 2269-2281.
17. H.-S. Wu, X.-F. Quin, X.-H. Xu, H. Jiao, P. von R. Schleyer, J. Am. Chem. Soc. 2005, 127, 2334-2338;
18. other strain measures are presented in references [13,19,20,23,29,32]; however, here we prefer the estimate with respect to dodecahedrane, although not completely strainless itself (cf. H.-D. Beckhaus, C. Rüchardt, D. R. Lagerwall, L. A. Paquette, F. Wahl, H. Prinzbach, J. Am. Chem. Soc. 1994, 116, 11775-11778) but setting its strain to zero gives strain energy consisting of Baeyer strain exclusively.
19. H. Hopf, Classics in Hydrocarbon Chemistry. Synthesis, Concepts, Perspectives; Wiley-VCH, Weinheim, 2000.
20. P. E. Eaton, T. W Cole, J. Am. Chem. Soc. 1964, 86, 3157-3158.
21. R. J. Ternansky, P. W. Balogh, L. A. Paquette, J. Am. Chem. Soc. 1982, 104, 4503-4504.
22. L. B. Rodewald, H. Lee, J. Am. Chem. Soc. 1973, 95, 623-625.
23. a) P. B. Shevlin, A. P. Wolf, J. Am. Chem. Soc. 1970, 92, 406-408;
24. b) R. F. Peterson, R. T. K. Baker, R. L. Wolfgang, Tetrahedron Lett. 1969, 10, 4749-4752.
25. H. W. Lage, H. P. Reisenauer, G. Maier, Tetrahedron Lett. 1982, 23, 3893-3896.
26. G. Maier, M. Hoppe, H. P. Reisenauer, Angew. Chem. 1983, 95, 1009-1010;
27. Angew. Chem. Int. Ed. Engl. 1983, 22, 990-991.
28. G. Maier, M. Hoppe, K. Lanz, H. P. Reisenauer, Tetrahedron Lett. 1984, 25, 5645-5648.
29. H. P. Reisenauer, cited in M. Christi, S. Freund, Chem. Ber. 1985, 118, 979-999.
30. D. A. Kaisaki, D. A. Dougherty, Tetrahedron Lett. 1987, 28, 5263-5266.
31. G. Maier, Angew. Chem. 1988, 700, 317-341;
32. Angew. Chem. Int. Ed. Engl. 1988, 27, 309-332.
33. H. Kollmar, J. Am. Chem. Soc. 1980, 702, 2617-2621.
34. N. C. Baird, M. J. S. Dewar, J. Am. Chem. Soc. 1967, 89, 3966-3970.
35. R. J. Buenker, S. D. Peyerimhoff, J. Am. Chem. Soc. 1969, 97, 4342-4346.
36. N. C. Baird, M. J. S. Dewar, J. Chem. Phys. 1969, 50, 1262-1274.
37. N. C. Baird, Tetrahedron 1970, 26, 2185-2190.
38. J. M. Schulman, T. J. Venanzi, J. Am. Chem. Soc. 1974, 96, 4739-4746.
39. W. J. Hehre, J. A. Pople, J. Am. Chem. Soc. 1975, 97, 6941 -6955.
40. M. C. Böhm, R. Gleiter, Tetrahedron Lett. 1978, 14, 1179-1182.
41. J. D. Dill, A. Greenberg, J. F. Liebman, J. Am. Chem. Soc. 1979, 707, 6814-6826.
42. H. Kollmar, F. Carrion, M. J. S. Dewar, R. C. Bingham, J. Am. Chem. Soc. 1981, 705, 5292-5303.
43. G. Fitzgerald, P. Saxe, H. F. Schaefer, J. Am. Chem. Soc. 1983, 705, 690-695.
44. R. L. Disch, J. M. Schulman, M. L. Sabio, J. Am. Chem. Soc. 1984, 106, 1904-1906.
45. B. A. Hess Jr., D. Michalska, L. J. Schaad, J. Am. Chem. Soc. 1985, 107, 1449-1450.
46. B. A. Hess Jr., W. D. Allen, D. Michalska, L. J. Schaad, H. F. Schaefer III, J. Am. Chem. Soc. 1987, 709, 1615-1621.
47. M. N. Glukhovtsev, S. Laiter, A. Pross, J. Phys. Chem. 1995, 99, 6828-6831.
48. D.W. Ball, J. Mol. Struct. 1996, 564, 183-188.
49. C. W. Earley, J. Phys. Chem. A 2000, 104, 6622-6627.
50. B. S. Jursic, J. Mol. Struct. 2000, 499, 137-140.
51. B. S. Jursic, J. Mol. Struct. 2000, 507, 185-192.
52. D. Moran, M. Manoharan, T. Heine, P. von R. Schleyer, Org. Lett. 2002, 4, 23-26.
53. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
54. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
55. a) J. Cizek, J. Chem. Phys. 1966, 45, 4256-4266;
56. b) J. Gauß in Encyclopedia of Computational Chemistry, Vol. 1, (Eds.: P. von R. Schleyer, N. L. Allinger, T. Clark, J. Gasteiger, A. P. Kollman, H. F. Schaefer III, P. R. Schreiner), Wiley, Chichester, 1998, pp. 615-636.
57. K. Raghavachari, G. W. Trucks, J. A. Pople, M. Head-Gordon, Chem. Phys. Lett. 1989, 757, 479-483.
58. D. E. Woon, T. H. Dunning Jr., J. Chem. Phys. 1993, 98, 1358-1371.
59. C. J. Cramer, Essentials of Computational Chemistry 2nd ed., Wiley, Chichester, 2004.
60. C. D. Sherrill, T. J. Van Huis, Y. Yamaguchi, H. F. Schaefer, J. Mol. Struct. 1997, 400, 139-156.
61. H. F. Bettinger, P. R. Schreiner, P. von R. Schleyer, H. F. Schaefer, Modern Electronic Structure Theory and Applications in Organic Chemistry, World Scientific, Singapore, 1997, pp. 183-196.
62. 1 values (see Supporting Information) exceed the critical limit of 0.02, the multideterminantal nature is of low importance for the description of all singlet carbenes and biradicaloid species discussed here.
63. P. R. Schreiner, A. Navarro-Vazquez, M. Prall, Acc. Chem. Res. 2005, 38, 29-37.
64. The details of apparatus and its uses are described in P. R. Schreiner, H. P. Reisenauer, ChemPhysChem 2006, 7, 880-885;
65. P. R. Schreiner, H. P. Reisenauer, W. D. Allen, K. W. Sattelmeyer, Org. Lett. 2004, 6, 1163-1166;
66. PR. Schreiner, H. P. Reisenauer, K. W. Sattelmeyer, W.D. Allen, J. Am. Chem. Soc. 2005, 727, 12156-12157.
67. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-869;
68. Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
69. 4: R. G. Pearson, Symmetry Rules for Chemical Reactions: Orbital Topology and Elementary Process, Wiley, New York, 1976.
70. A. Hirsch, Z. Chen, H. Jiao, Angew. Chem. 2001, 113, 2916-2920;
71. Angew. Chem. Int. Ed. 2001, 40, 2834-2838.
72. A.A. Fokin, B. Kiran, M. Bremer, X. Yang, H. Jiao, P. von R. Schleyer, P. R. Schreiner, Chem. Eur. J. 2000, 6, 1615-1628.
73. D. Cremer, E. Kraka, J. Am. Chem. Soc. 1985, 707, 3800-3810.
74. Y. Mo, Org. Lett. 2006, 8, 535-538.
75. F. Jensen, Introduction to Computational Chemistry, 1st ed., Wiley, Chichester, 2004.
76. For IR-spectra in Ar matrices: of 4 and 5 see: G. Maier, M. Hoppe, K. Lanz, H. P. Reisenauer, Tetrahedron Lett. 1984, 25, 5645-56458;
77. for 2 see: W. E. Billups, L-J. Lin, E. W. Casserly, J. Am. Chem. Soc. 1984, 706, 3698-3699.
78. R. Wrobel, W. Sander, D. Cremer, E. Kraka, J. Phys. Chem. A 2000, 104, 3819-3825.
79. A. D. Walsh, J. Chem. Soc. 1953, 2260-2266.
80. M. Yoshimine, J. Pacansky, N. Honjou, J. Am. Chem. Soc. 1989, 111, 2785-2798.
81. K. M. Ervin, J. Ho, W. C. Lineberger, J. Chem. Phys. 1989, 97, 5974-5992.
82. N. Balucani, A. M. Mebel, Y. T. Lee, R. I. Kaiser, J. Phys. Chem. A 2001, 705, 9813-9818, and references therein
83. R. P. Johnson, K. J. Dadoust, J. Am. Chem. Soc. 1995, 777, 362-367, and references therein
84. H.-U. Wagner, G. Szeimies, J. Chandrasekhar, P. von R. Schleyer, J. A. Pople, J. Binkley, J. Am. Chem. Soc. 1978, 700, 1210-1213.