Dichlorocarbene addition to [5]metacyclophane; experimental and calculational evidence for a [1,5] sigmatropic chlorine shift in a bridged cycloheptatriene

Journal of Organic Chemistry

Volumn 65, Issue 14, 2000, Pages 4348-4354

  Van Eis, Maurice J ^a   Van Der Linde, Barbara S E ^a   De Kanter, Franciscus J J ^a   De Wolf, Willem H ^a   Bickelhaupt, Friedrich ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CHLORINE; CYCLOHEPTANE DERIVATIVE; METACYCLOPHANE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL BOND; COMPLEX FORMATION; ISOMERISM; REACTION ANALYSIS;

EID: 0034647909     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000197d     Document Type: Article

References (60)

1. For recent reviews, see: (a) Bodwell, G. J. Angew. Chem. 1996, 108, 2221; Angew. Chem., Int. Ed. Eng. 1996, 35, 2085. (b) Bickelhaupt, F.; de Wolf, W. H. J. Phys. Org. Chem. 1998, 11, 362. (c) Tsuji, T. In Advances in Strain and Interesting Organic Molecules; Halton. B., Ed.; JAI Press: Stamford, 1999; Vol. 7, 103-152.
2. For recent reviews, see: (a) Bodwell, G. J. Angew. Chem. 1996, 108, 2221; Angew. Chem., Int. Ed. Eng. 1996, 35, 2085. (b) Bickelhaupt, F.; de Wolf, W. H. J. Phys. Org. Chem. 1998, 11, 362. (c) Tsuji, T. In Advances in Strain and Interesting Organic Molecules; Halton. B., Ed.; JAI Press: Stamford, 1999; Vol. 7, 103-152.
3. For recent reviews, see: (a) Bodwell, G. J. Angew. Chem. 1996, 108, 2221; Angew. Chem., Int. Ed. Eng. 1996, 35, 2085. (b) Bickelhaupt, F.; de Wolf, W. H. J. Phys. Org. Chem. 1998, 11, 362. (c) Tsuji, T. In Advances in Strain and Interesting Organic Molecules; Halton. B., Ed.; JAI Press: Stamford, 1999; Vol. 7, 103-152.
4. For recent reviews, see: (a) Bodwell, G. J. Angew. Chem. 1996, 108, 2221; Angew. Chem., Int. Ed. Eng. 1996, 35, 2085. (b) Bickelhaupt, F.; de Wolf, W. H. J. Phys. Org. Chem. 1998, 11, 362. (c) Tsuji, T. In Advances in Strain and Interesting Organic Molecules; Halton. B., Ed.; JAI Press: Stamford, 1999; Vol. 7, 103-152.
5. (a) Tsuji, T.; Ohkita, M.; Konno, T.; Nishida S. J. Am. Chem. Soc. 1997, 119, 8425.
6. (b) Kawai, H.; Suzuki, T.; Ohkita, M.; Tsuji, T. Angew. Chem. 1998, 110, 827; Angew. Chem., Int. Ed. Engl. 1998, 37, 817.
7. (b) Kawai, H.; Suzuki, T.; Ohkita, M.; Tsuji, T. Angew. Chem. 1998, 110, 827; Angew. Chem., Int. Ed. Engl. 1998, 37, 817.
8. Van Eis, M. J.; Komen, C. M. D.; de Kanter, F. J. J.; de Wolf, W. H.; Lammertsma, K.; Bickelhaupt, F.; Lutz, M.; Spek, A. Angew. Chem. 1998, 110, 1656; Angew. Chem., Int. Ed. Engl. 1998, 37, 1547.
9. Van Eis, M. J.; Komen, C. M. D.; de Kanter, F. J. J.; de Wolf, W. H.; Lammertsma, K.; Bickelhaupt, F.; Lutz, M.; Spek, A. Angew. Chem. 1998, 110, 1656; Angew. Chem., Int. Ed. Engl. 1998, 37, 1547.
10. Ciganek, E. J. Am. Chem. Soc. 1967, 89, 1454.
11. (a) Murray, R. W. Tetrahedron Lett. 1960, 27.
12. (b) Blume, G.; Neumann, T.; Weyerstahl, P. Justus Liebigs Ann. Chem. 1975, 201.
13. (a) Thummel, R. P.; Chayangkoon, P. Tetrahedron Lett. 1984, 5601.
14. (b) Königstein, V. Tochtermann, W. Tetrahedron Lett. 1986, 2961.
15. For a review on sigmatropic rearrangements, see: Sprangler, C. W. Chem. Rev. 1976, 76, 187.
16. For examples of experimental and semiempirical studies on chlorine migrations, see: (a) Hartshorn, M. P.; Hayman, K. A.; Martyn, R. J.; Robinson, W. T.; Vaughan, J.; Wells, B. A.; Wright, G. J. Aust. J. Chem. 1990, 43, 1729. (b) Popkova, V. Y.; Ansimv, V. M.; Dolenko, G. N.; Semenenko, M. N.; Fedoseev, V. M. J. Chem. Soc., Perkin Trans. 2 1995, 1375. (c) Mikailov, I. E.; Dushenko, G. A.; Kisin, A. V.; Mügge, C.; Zschunke, A.; Minkin, V. I. Mendeleev Commun. 1994, 85. (d) Samarai, L. J.; Gorbatenko, V. I.; Boldeskul, I. E.; Luk'yanchuk, V. P. Zh. Org. Khim. 1976, 12, 547. (e) König, K.-H.; Feuerherd, K.-H.; Schwendemann, V. M.; Oeser, H.-G. Angew. Chem., Int. Ed. Engl. 1981, 20, 883.
17. For examples of experimental and semiempirical studies on chlorine migrations, see: (a) Hartshorn, M. P.; Hayman, K. A.; Martyn, R. J.; Robinson, W. T.; Vaughan, J.; Wells, B. A.; Wright, G. J. Aust. J. Chem. 1990, 43, 1729. (b) Popkova, V. Y.; Ansimv, V. M.; Dolenko, G. N.; Semenenko, M. N.; Fedoseev, V. M. J. Chem. Soc., Perkin Trans. 2 1995, 1375. (c) Mikailov, I. E.; Dushenko, G. A.; Kisin, A. V.; Mügge, C.; Zschunke, A.; Minkin, V. I. Mendeleev Commun. 1994, 85. (d) Samarai, L. J.; Gorbatenko, V. I.; Boldeskul, I. E.; Luk'yanchuk, V. P. Zh. Org. Khim. 1976, 12, 547. (e) König, K.-H.; Feuerherd, K.-H.; Schwendemann, V. M.; Oeser, H.-G. Angew. Chem., Int. Ed. Engl. 1981, 20, 883.
18. For examples of experimental and semiempirical studies on chlorine migrations, see: (a) Hartshorn, M. P.; Hayman, K. A.; Martyn, R. J.; Robinson, W. T.; Vaughan, J.; Wells, B. A.; Wright, G. J. Aust. J. Chem. 1990, 43, 1729. (b) Popkova, V. Y.; Ansimv, V. M.; Dolenko, G. N.; Semenenko, M. N.; Fedoseev, V. M. J. Chem. Soc., Perkin Trans. 2 1995, 1375. (c) Mikailov, I. E.; Dushenko, G. A.; Kisin, A. V.; Mügge, C.; Zschunke, A.; Minkin, V. I. Mendeleev Commun. 1994, 85. (d) Samarai, L. J.; Gorbatenko, V. I.; Boldeskul, I. E.; Luk'yanchuk, V. P. Zh. Org. Khim. 1976, 12, 547. (e) König, K.-H.; Feuerherd, K.-H.; Schwendemann, V. M.; Oeser, H.-G. Angew. Chem., Int. Ed. Engl. 1981, 20, 883.
19. For examples of experimental and semiempirical studies on chlorine migrations, see: (a) Hartshorn, M. P.; Hayman, K. A.; Martyn, R. J.; Robinson, W. T.; Vaughan, J.; Wells, B. A.; Wright, G. J. Aust. J. Chem. 1990, 43, 1729. (b) Popkova, V. Y.; Ansimv, V. M.; Dolenko, G. N.; Semenenko, M. N.; Fedoseev, V. M. J. Chem. Soc., Perkin Trans. 2 1995, 1375. (c) Mikailov, I. E.; Dushenko, G. A.; Kisin, A. V.; Mügge, C.; Zschunke, A.; Minkin, V. I. Mendeleev Commun. 1994, 85. (d) Samarai, L. J.; Gorbatenko, V. I.; Boldeskul, I. E.; Luk'yanchuk, V. P. Zh. Org. Khim. 1976, 12, 547. (e) König, K.-H.; Feuerherd, K.-H.; Schwendemann, V. M.; Oeser, H.-G. Angew. Chem., Int. Ed. Engl. 1981, 20, 883.
20. For examples of experimental and semiempirical studies on chlorine migrations, see: (a) Hartshorn, M. P.; Hayman, K. A.; Martyn, R. J.; Robinson, W. T.; Vaughan, J.; Wells, B. A.; Wright, G. J. Aust. J. Chem. 1990, 43, 1729. (b) Popkova, V. Y.; Ansimv, V. M.; Dolenko, G. N.; Semenenko, M. N.; Fedoseev, V. M. J. Chem. Soc., Perkin Trans. 2 1995, 1375. (c) Mikailov, I. E.; Dushenko, G. A.; Kisin, A. V.; Mügge, C.; Zschunke, A.; Minkin, V. I. Mendeleev Commun. 1994, 85. (d) Samarai, L. J.; Gorbatenko, V. I.; Boldeskul, I. E.; Luk'yanchuk, V. P. Zh. Org. Khim. 1976, 12, 547. (e) König, K.-H.; Feuerherd, K.-H.; Schwendemann, V. M.; Oeser, H.-G. Angew. Chem., Int. Ed. Engl. 1981, 20, 883.
21. Koch, R.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 61, 6809.
22. Looker, J. J. J. Org. Chem. 1972, 37, 1059.
23. Feigel, M.; Kessler, H. Tetrahedron 1976, 32, 1575.
24. (a) Ter Borg, A. P.; Kloosterziel, H. Rec. Trav. Chem. 1963, 82, 741.
25. (b) Murry, R. W.; Kaplan, H. L. J. Am. Chem. Soc. 1966, 88, 3527.
26. (c) Mukai, T.; Kubota, H.; Toda, T. Tetrahedron Lett. 1967, 37, 3581.
27. (d) Ashe, A. J., III. J. Org. Chem. 1972, 37, 2053. Larrabee, R. B. J. Organomet. Chem. 1974, 74, 313.
28. (d) Ashe, A. J., III. J. Org. Chem. 1972, 37, 2053. Larrabee, R. B. J. Organomet. Chem. 1974, 74, 313.
29. (f) Shono, T.; Maekawa, H.; Nozoe, T.; Kashimura, S. Tetrahedron Lett. 1990, 31, 895.
30. (a) Larrabee, R. B. J. Am. Chem. Soc. 1971, 93, 1510.
31. (b) Curtis, M. D.; Fink, R. J. Organomet. Chem. 1972, 38, 299.
32. (c) Mann, B. E.; Taylor, B. F.; Taylor, N. A.; Wood, R. J. Organomet. Chem. 1978, 162, 137.
33. (d) Gridnev, I. D.; Schreiner, P. R.; Tok, O. L.; Bubnov, Y. N.; Chem. Eur. J. 1999, 5, 2828.
34. Gridnev, I. D.; Tok, O. L.; Gridneva, N. A.; Bubnov, Y. N.; Schreiner, P. R. J. Am. Chem. Soc. 1998, 120, 1034.
35. (a) Gilheany, D. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons Ltd: London, 1990; Vol. 1, pp 9-49.
36. (b) CRC Handbook of Chemistry and Physics, 1 Student Edition; Weast, R. C., Ed.; CRC Press: Boca Raton, Florida, 1988; F-106.
37. Rubin, M. B. J. Am. Chem. Soc. 1981, 103, 7791.
38. (a) Jorgensen, W. L. J. Am. Chem. Soc. 1976, 98, 6784.
39. (b) Cremer, D.; Dick, B. Angew. Chem. 1982, 94, 877; Angew. Chem., Int. Ed. Engl. 1982, 21, 865.
40. (b) Cremer, D.; Dick, B. Angew. Chem. 1982, 94, 877; Angew. Chem., Int. Ed. Engl. 1982, 21, 865.
41. (c) Schulman, J. M.; Disch, R. L.; Sabio, M. L. J. Am. Chem. Soc. 1984, 106, 7696.
42. Butcher, S. S. J. Chem. Phys. 1965, 42, 1833.
43. (a) Jensen, F. R.; Smith, L. A. J. Am. Chem. Soc. 1964, 86, 956.
44. (b) Anet, F. A. L. J. Am. Chem. Soc. 1964, 86, 458.
45. (a) Schulman, J. M.; Dish, R. L.; Sabio, M. L. J. Am. Chem. Soc. 1982, 104, 3785.
46. (b) Kao, J. J. Am. Chem. Soc. 1987, 109, 3817.
47. (c) Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
48. (d) Donovan, W. H.; White, W. E. J. Org. Chem. 1996, 61, 969.
49. Roth, W. R.; Klärner, F.-G.; Siepert, G.; Lennartz, H.-W. Chem. Ber. 1992, 125, 217.
50. (a) Van Straten, J. W.; De Wolf, W. H.; Bickelhaupt, F. Tetrahedron Lett. 1977, 4667.
51. (b) Recently the synthesis of 1 has been markedly improved. Van Eis, M. J.; Wijsman, G. W.; De Wolf, W. H.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. Chem. Eur. J. 2000, 6, 1537.
52. Tomoda, S.; Takamatsu, K.; Iwaoka, M. Chem. Lett. 1998, 581. We thank a referee for drawing our attention to this reference.
53. Keating, A. E.; Merrigan, S. R.; Singleton, D. A.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 3933 and references therein.
54. Nordlander, J. E.; Owuor, P. O.; Haky, J. E. J. Am. Chem. Soc. 1979, 101, 188.
55. Cerius2, Version 3.5, Software Environment for Chemical Computing, Molecular Simulations Inc.
56. All B3LYP/6-31G* calculations were performed with the Gaussian 98 suite of programs: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; and Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1998.
57. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
58. Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785.
59. Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1.
60. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. Chem. Phys. Lett. 1997, 270, 419.