The cyclization of parent and cyclic hexa-1,3-dien-5-ynes - A combined theoretical and experimental study

Chemistry - A European Journal

Volumn 7, Issue 20, 2001, Pages 4386-4394

  Prall, Matthias ^a   Krüger, Anke ^b   Schreiner, Peter R ^a,c   Hopf, Henning ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^c UNIVERSITY OF GEORGIA   (United States)

Author keywords

Ab initio calculations; Cycloaromatization; Enynes; Isobenzene; Macrocycles

Indexed keywords

AROMATIC HYDROCARBONS; MOLECULAR STRUCTURE;

CYCLIZATION;

ISOMERIZATION;

ALLENE DERIVATIVE; BENZENE; BENZENE DERIVATIVE; CYCLOALKENE; HEXA 1,3 DIEN 5 YNE DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; ENANTIOMER; ISOMERISM; PHASE TRANSITION; TEMPERATURE DEPENDENCE;

EID: 0035887050     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011015)7:20<4386::AID-CHEM4386>3.0.CO;2-S     Document Type: Article

References (73)

1. L. T. Scott, M. M. Hashemi, D. T. Meyer, H. B. Warren, J. Am. Chem. Soc. 1991, 113, 7082-7084.
2. L. T. Scott, P.-C. Cheng, M. M. Hashemi, M. S. Bratcher, D. T. Meyer, H. B. Warren, J. Am. Chem. Soc. 1997, 119, 10963-10968.
3. G. Zimmermann, U. Nüchter, S. Hagen, M. Nüchter, Tetrahedron Lett. 1994, 35, 4747-4750.
4. P. W. Rabideau, A. H. Abdourazak, H. E. Folsom, Z. Marcinow, A. Sygula, R. Sygula, J. Am. Chem. Soc. 1994, 116, 7891-7892.
5. H. Hopf, H. Musso, Angew. Chem. 1969, 81, 704;
6. Angew. Chem. Int. Ed. Engl. 1969, 8, 680.
7. W. R. Roth, H. Hopf, C. Horn, Chem. Ber. 1994, 127, 1765-1779.
8. W. R. Roth, H. Hopf, C. Horn, Chem. Ber. 1994, 127, 1781-1795.
9. H. Hopf, H. Berger, G. Zimmermann, U. Nüchter, P. G. Jones, I. Dix, Angew. Chem. 1997, 109, 1236-1238;
10. Angew. Chem. Int. Ed. Engl. 1997, 36, 1187-1190.
11. M. Christl, S. Groetsch, Eur. J. Org. Chem. 2000, 1871-1874.
12. M. Christl, S. Drinkuth, Eur. J. Org. Chem. 1998, 237-241.
13. G. Zimmermann, M. Nüchter, M. Remmler, M. Findeisen, H. Hopf, L. Ernst, C. Mlynek, Chem. Ber. 1994, 127, 1747-1753.
14. U. Nüchter, G. Zimmermann, V. Francke, H. Hopf, Liebigs Ann./ Recueil 1997, 1505-1515.
15. K. Schulz, J. Hofmann, G. Zimmermann, Liebigs Ann./Recueil 1997, 2535-2539.
16. J. Hofmann, K. Schulz, A. Altmann, M. Findeisen, G. Zimmermann, Liebigs Ann./Recueil 1997, 2541-2548.
17. G. Zimmermann, Eur. J. Org. Chem. 2001, 457-471.
18. S. Koseki, Y. Fujimura, M. Hirama, J. Phys. Chem. A 1999, 103, 7672-7675.
19. T. Kaneko, M. Takahashi, M. Hirama, Tetrahedron Lett. 1999, 40, 2015-2018.
20. W.-H. Chen, N.-Y. Chang, C.-H. Yu, J. Phys. Chem. 1998, 102, 2584-2593.
21. W. R. Roth, H. Hopf, T. Wasser, H. Zimmermann, C. Werner, Liebigs Ann. 1996, 1691-1695.
22. M. Prall, A. Wittkopp, P. R. Schreiner, J. Phys. Chem. 2001, in press.
23. P. R. Schreiner, Chem. Commun. 1998, 4, 483-484.
24. P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190.
25. N. Hanold, H. Meier, Chem. Ber. 1985, 118, 198-209.
26. H. Meier, N. Hanold, H. Kolshorn, Angew. Chem. 1982, 94, 67-68;
27. Angew. Chem. Int. Ed. Engl. 1982, 21, 66-67.
28. M. Hanack, R. Rieth, J. Chem. Soc. Chem. Commun. 1985, 21, 1487-1489.
29. M. Hanack, R. Rieth, Chem. Ber. 1987, 120, 1659-1666.
30. Gaussian 98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998
31. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100.
32. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
33. B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 1989, 157, 200-216.
34. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
35. P. C. Hariharan, J. A. Pople, Theoret. Chimica Acta 1973, 28, 213-222.
36. K. A. Brueckner, Phys. Rev. 1954, 96, 508-516.
37. C. E. Dykstra, Chem. Phys. Lett. 1977, 45, 466-469.
38. N. C. Handy, J. A. Pople, M. Head-Gordon, K. Raghavachari, G. W. Trucks, Chem. Phys. Lett. 1989, 164, 185-192.
39. K. Raghavachari, G. W. Trucks, J. A. Pople, M. Head-Gordon, Chem. Phys. Lett. 1989, 157, 479-483.
40. R. J. Bartlett, J. D. Watts, S. A. Kucharski, J. Noga, J. Chem. Phys. Lett. 1989, 165, 513-522.
41. T. H. Dunning, J. Chem. Phys. 1989, 90, 1007-1023.
42. H. F. Bettinger, P. v. R. Schleyer, P. R. Schreiner, H. F. Schaefer III in Computational Analyses of Prototype Carbene Structures and Reactions (Ed.: E. L. Davidson), World Scientific, Singapore, 1997, pp. 89-171.
43. C. J. Cramer, M. A. Hillmyer, J. Org. Chem. 1999, 64, 4850-4859.
44. S. E. Worthington, C. J. Cramer, J. Phys. Org. Chem. 1997, 10, 755-767.
45. P. G. Wenthold, M. A. Lipton, J. Am. Chem. Soc. 2000, 122, 9265-9270.
46. P. G. Wenthold, J. Chem. Soc. Perkin Trans. 2 1999, 11, 2357-2363.
47. B. Engels, M. Hanrath, C. Lennartz, Comput. Chem. 2001, 25, 15-38.
48. C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269.
49. J. Gräfenstein, A. M. Hjerpe, E. Kraka, D. Cremer, J. Phys. Chem. A 2000, 104, 1748-1761.
50. P. R. Schreiner, M. Prall, J. Am. Chem. Soc. 1999, 121, 8615-8627.
51. H. F. Bettinger, P. R. Schreiner, H. F. Schaefer III, P. v. R. Schleyer, J. Am. Chem. Soc. 1998, 120, 5741-5750.
52. E. Kraka, D. Cremer, J. Am. Chem. Soc. 2000, 122, 8245-8264.
53. G. B. Jones, P. M. Warner, J. Am. Chem. Soc. 2001, 123, 2134-2145.
54. W. T. G. Johnson, C. J. Cramer, J. Am. Chem. Soc. 2001, 123, 923-928.
55. C. J. Cramer, J. Thompson, J. Phys. Chem. A 2001, 105, 2091-2098.
56. J. Hoffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385.
57. M. Christl, M. Braun, G. Müller, Angew. Chem. 1992, 104, 471-473;
58. Angew. Chem. Int. Ed. Engl. 1992, 31, 473-476.
59. R. Janoschek, Angew. Chem. 1992, 104, 473-475;
60. Angew. Chem. Int. Ed. Engl. 1992, 31, 476-478.
61. A. Navarro-Vázquez, D. Rodríguez, L. Castedo, D. Domínguez, C. Saá, personal communication 2001.
62. P. M. W. Gill, Mol. Phys. 1996, 89, 433-445.
63. J. P. Perdew, Y. Wang, Phys. Rev. B 1992, 45 (23), 13244-13249.
64. R. McWeeny, G. Dierksen, J. Chem. Phys. 1968, 49, 4852-4856.
65. J. A. Pople, R. K. Nesbet, J. Chem. Phys. 1954, 23, 571-574.
66. C. C. J. Roothan, Rev. Mod. Phys. 1951, 23, 69-89.
67. C. Møller, M. S. Plesset, Phys. Rev. 1934, 46, 618-622.
68. R. H. E. Eade, M. A. Robb, Chem. Phys. Lett. 1981, 83, 362-368.
69. D. Hegarty, M. A. Robb, Mol. Phys. 1979, 38, 1795-1812.
70. P. R. Schreiner, W. L. Karney, P. v. R. Schleyer, W. T. Borden, T. P. Hamilton, H. F. Schaefer III, J. Org. Chem. 1996, 61, 7030-7039.
71. M. W. Wong, C. Wentrup, J. Org. Chem. 1996, 61, 7022-7029.
72. S. Matzinger, T. Bally, E. V. Patterson, R. J. McMahon, J. Am. Chem. Soc. 1996, 118, 1535-1542.
73. H. Hopf, A. Krüger, Chem. Eur. J. 2001, 7, 4378-4385.