Electrocyclic ring opening modes of Dewar benzenes: Ab initio predictions for Mobius benzene and trans-Dewar benzene as new C6H6 isomers

Journal of the American Chemical Society

Volumn 118, Issue 31, 1996, Pages 7381-7385

  Johnson, Richard P ^a   Daoust, Kimberly J ^a  

^a Univ of New Hampshire   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE;

ARTICLE; ELECTROCHEMISTRY; REACTION ANALYSIS;

EID: 0029739929     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961066q     Document Type: Article

References (60)

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2. For discussions of benzene isomers, see: (a) Cutman, I.; Potgeiter, J. H. J. Chem. Educ. 1994, 71, 222 (b) Rogers, D. W.; McLafferty, F. J.; Fang, W.; Qi, Y. Struct. Chem. 1993, 4, 161. (c) Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc. 1985, 107, 5059. (d) Kobayashi, K.; Itsumaro, K. Top. Curr. Chem. 1984, 123, 103. (e) Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978. (f) Newton, M. D.; Schulman, J. M.; Manus, M. M. J. Am. Chem. Soc. 1974, 96, 17. (g) Greenberg, A.; Liebman, J. F. Tetrahedron 1979, 35, 2623.
3. For discussions of benzene isomers, see: (a) Cutman, I.; Potgeiter, J. H. J. Chem. Educ. 1994, 71, 222 (b) Rogers, D. W.; McLafferty, F. J.; Fang, W.; Qi, Y. Struct. Chem. 1993, 4, 161. (c) Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc. 1985, 107, 5059. (d) Kobayashi, K.; Itsumaro, K. Top. Curr. Chem. 1984, 123, 103. (e) Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978. (f) Newton, M. D.; Schulman, J. M.; Manus, M. M. J. Am. Chem. Soc. 1974, 96, 17. (g) Greenberg, A.; Liebman, J. F. Tetrahedron 1979, 35, 2623.
4. For discussions of benzene isomers, see: (a) Cutman, I.; Potgeiter, J. H. J. Chem. Educ. 1994, 71, 222 (b) Rogers, D. W.; McLafferty, F. J.; Fang, W.; Qi, Y. Struct. Chem. 1993, 4, 161. (c) Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc. 1985, 107, 5059. (d) Kobayashi, K.; Itsumaro, K. Top. Curr. Chem. 1984, 123, 103. (e) Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978. (f) Newton, M. D.; Schulman, J. M.; Manus, M. M. J. Am. Chem. Soc. 1974, 96, 17. (g) Greenberg, A.; Liebman, J. F. Tetrahedron 1979, 35, 2623.
5. For discussions of benzene isomers, see: (a) Cutman, I.; Potgeiter, J. H. J. Chem. Educ. 1994, 71, 222 (b) Rogers, D. W.; McLafferty, F. J.; Fang, W.; Qi, Y. Struct. Chem. 1993, 4, 161. (c) Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc. 1985, 107, 5059. (d) Kobayashi, K.; Itsumaro, K. Top. Curr. Chem. 1984, 123, 103. (e) Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978. (f) Newton, M. D.; Schulman, J. M.; Manus, M. M. J. Am. Chem. Soc. 1974, 96, 17. (g) Greenberg, A.; Liebman, J. F. Tetrahedron 1979, 35, 2623.
6. For discussions of benzene isomers, see: (a) Cutman, I.; Potgeiter, J. H. J. Chem. Educ. 1994, 71, 222 (b) Rogers, D. W.; McLafferty, F. J.; Fang, W.; Qi, Y. Struct. Chem. 1993, 4, 161. (c) Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc. 1985, 107, 5059. (d) Kobayashi, K.; Itsumaro, K. Top. Curr. Chem. 1984, 123, 103. (e) Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978. (f) Newton, M. D.; Schulman, J. M.; Manus, M. M. J. Am. Chem. Soc. 1974, 96, 17. (g) Greenberg, A.; Liebman, J. F. Tetrahedron 1979, 35, 2623.
7. For discussions of benzene isomers, see: (a) Cutman, I.; Potgeiter, J. H. J. Chem. Educ. 1994, 71, 222 (b) Rogers, D. W.; McLafferty, F. J.; Fang, W.; Qi, Y. Struct. Chem. 1993, 4, 161. (c) Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc. 1985, 107, 5059. (d) Kobayashi, K.; Itsumaro, K. Top. Curr. Chem. 1984, 123, 103. (e) Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978. (f) Newton, M. D.; Schulman, J. M.; Manus, M. M. J. Am. Chem. Soc. 1974, 96, 17. (g) Greenberg, A.; Liebman, J. F. Tetrahedron 1979, 35, 2623.
8. Benzene photoisomerization: (a) Bryce-Smith, D.; A. Tetrahedron 1976, 32, 1309; 1977, 33, 2459. (b) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific Publications: Boston, 1991. (c) Bryce-Smith, D.; Gilbert, A. Rearrangements in Ground and Excited Slates; Demayo, P., Ed.; Academic Press: New York, 1980; Vol. 3. (d) Ivanoff, M. N.; Lahmani, F. In Eléments de Photochimie Avancée; Courtot, P. , Ed.; Hermann: Paris, 1972.
9. Benzene photoisomerization: (a) Bryce-Smith, D.; A. Tetrahedron 1976, 32, 1309; 1977, 33, 2459. (b) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific Publications: Boston, 1991. (c) Bryce-Smith, D.; Gilbert, A. Rearrangements in Ground and Excited Slates; Demayo, P., Ed.; Academic Press: New York, 1980; Vol. 3. (d) Ivanoff, M. N.; Lahmani, F. In Eléments de Photochimie Avancée; Courtot, P. , Ed.; Hermann: Paris, 1972.
10. Benzene photoisomerization: (a) Bryce-Smith, D.; A. Tetrahedron 1976, 32, 1309; 1977, 33, 2459. (b) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific Publications: Boston, 1991. (c) Bryce-Smith, D.; Gilbert, A. Rearrangements in Ground and Excited Slates; Demayo, P., Ed.; Academic Press: New York, 1980; Vol. 3. (d) Ivanoff, M. N.; Lahmani, F. In Eléments de Photochimie Avancée; Courtot, P. , Ed.; Hermann: Paris, 1972.
11. Benzene photoisomerization: (a) Bryce-Smith, D.; A. Tetrahedron 1976, 32, 1309; 1977, 33, 2459. (b) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific Publications: Boston, 1991. (c) Bryce-Smith, D.; Gilbert, A. Rearrangements in Ground and Excited Slates; Demayo, P., Ed.; Academic Press: New York, 1980; Vol. 3. (d) Ivanoff, M. N.; Lahmani, F. In Eléments de Photochimie Avancée; Courtot, P. , Ed.; Hermann: Paris, 1972.
12. Benzene photoisomerization: (a) Bryce-Smith, D.; A. Tetrahedron 1976, 32, 1309; 1977, 33, 2459. (b) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific Publications: Boston, 1991. (c) Bryce-Smith, D.; Gilbert, A. Rearrangements in Ground and Excited Slates; Demayo, P., Ed.; Academic Press: New York, 1980; Vol. 3. (d) Ivanoff, M. N.; Lahmani, F. In Eléments de Photochimie Avancée; Courtot, P. , Ed.; Hermann: Paris, 1972.
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27. Experimental evidence: (a) Kropp, P. J.; Fravel, H. G., Jr.; Fields, T. R. J. Am. Chem. Soc. 1976, 98, 840. (b) Inoue, Y.; Takamuku, S.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1977, 1635. (c) Dauben, W. G.; vanRiel, H. C. H. A.; Robbins, J. D.; Wagner, G. J. J. Am. Chem. Soc. 1979, 101, 6383, (d) Inoue, Y.; Matsumoto, N.; Hakushi, T.; Srinivasan, R. J. Org. Chem. 1981, 46, 2267. (e) Saltiel, J.; Marchand, G. R.; Bonneau, R. J. Photochem. 1985, 28, 367. (f) Goodman, J. L.; Peters, K. S.; Misawa, H.; Caldwell, R. A. J. Am. Chem. Soc. 1986, 108, 6803. (g) Strickland, A. D.; Caldwell, R. A. J. Phys. Chem. 1993, 97, 13394.
28. Experimental evidence: (a) Kropp, P. J.; Fravel, H. G., Jr.; Fields, T. R. J. Am. Chem. Soc. 1976, 98, 840. (b) Inoue, Y.; Takamuku, S.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1977, 1635. (c) Dauben, W. G.; vanRiel, H. C. H. A.; Robbins, J. D.; Wagner, G. J. J. Am. Chem. Soc. 1979, 101, 6383, (d) Inoue, Y.; Matsumoto, N.; Hakushi, T.; Srinivasan, R. J. Org. Chem. 1981, 46, 2267. (e) Saltiel, J.; Marchand, G. R.; Bonneau, R. J. Photochem. 1985, 28, 367. (f) Goodman, J. L.; Peters, K. S.; Misawa, H.; Caldwell, R. A. J. Am. Chem. Soc. 1986, 108, 6803. (g) Strickland, A. D.; Caldwell, R. A. J. Phys. Chem. 1993, 97, 13394.
29. Experimental evidence: (a) Kropp, P. J.; Fravel, H. G., Jr.; Fields, T. R. J. Am. Chem. Soc. 1976, 98, 840. (b) Inoue, Y.; Takamuku, S.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1977, 1635. (c) Dauben, W. G.; vanRiel, H. C. H. A.; Robbins, J. D.; Wagner, G. J. J. Am. Chem. Soc. 1979, 101, 6383, (d) Inoue, Y.; Matsumoto, N.; Hakushi, T.; Srinivasan, R. J. Org. Chem. 1981, 46, 2267. (e) Saltiel, J.; Marchand, G. R.; Bonneau, R. J. Photochem. 1985, 28, 367. (f) Goodman, J. L.; Peters, K. S.; Misawa, H.; Caldwell, R. A. J. Am. Chem. Soc. 1986, 108, 6803. (g) Strickland, A. D.; Caldwell, R. A. J. Phys. Chem. 1993, 97, 13394.
30. Experimental evidence: (a) Kropp, P. J.; Fravel, H. G., Jr.; Fields, T. R. J. Am. Chem. Soc. 1976, 98, 840. (b) Inoue, Y.; Takamuku, S.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1977, 1635. (c) Dauben, W. G.; vanRiel, H. C. H. A.; Robbins, J. D.; Wagner, G. J. J. Am. Chem. Soc. 1979, 101, 6383, (d) Inoue, Y.; Matsumoto, N.; Hakushi, T.; Srinivasan, R. J. Org. Chem. 1981, 46, 2267. (e) Saltiel, J.; Marchand, G. R.; Bonneau, R. J. Photochem. 1985, 28, 367. (f) Goodman, J. L.; Peters, K. S.; Misawa, H.; Caldwell, R. A. J. Am. Chem. Soc. 1986, 108, 6803. (g) Strickland, A. D.; Caldwell, R. A. J. Phys. Chem. 1993, 97, 13394.
31. Experimental evidence: (a) Kropp, P. J.; Fravel, H. G., Jr.; Fields, T. R. J. Am. Chem. Soc. 1976, 98, 840. (b) Inoue, Y.; Takamuku, S.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1977, 1635. (c) Dauben, W. G.; vanRiel, H. C. H. A.; Robbins, J. D.; Wagner, G. J. J. Am. Chem. Soc. 1979, 101, 6383, (d) Inoue, Y.; Matsumoto, N.; Hakushi, T.; Srinivasan, R. J. Org. Chem. 1981, 46, 2267. (e) Saltiel, J.; Marchand, G. R.; Bonneau, R. J. Photochem. 1985, 28, 367. (f) Goodman, J. L.; Peters, K. S.; Misawa, H.; Caldwell, R. A. J. Am. Chem. Soc. 1986, 108, 6803. (g) Strickland, A. D.; Caldwell, R. A. J. Phys. Chem. 1993, 97, 13394.
32. Experimental evidence: (a) Kropp, P. J.; Fravel, H. G., Jr.; Fields, T. R. J. Am. Chem. Soc. 1976, 98, 840. (b) Inoue, Y.; Takamuku, S.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1977, 1635. (c) Dauben, W. G.; vanRiel, H. C. H. A.; Robbins, J. D.; Wagner, G. J. J. Am. Chem. Soc. 1979, 101, 6383, (d) Inoue, Y.; Matsumoto, N.; Hakushi, T.; Srinivasan, R. J. Org. Chem. 1981, 46, 2267. (e) Saltiel, J.; Marchand, G. R.; Bonneau, R. J. Photochem. 1985, 28, 367. (f) Goodman, J. L.; Peters, K. S.; Misawa, H.; Caldwell, R. A. J. Am. Chem. Soc. 1986, 108, 6803. (g) Strickland, A. D.; Caldwell, R. A. J. Phys. Chem. 1993, 97, 13394.
33. Experimental evidence: (a) Kropp, P. J.; Fravel, H. G., Jr.; Fields, T. R. J. Am. Chem. Soc. 1976, 98, 840. (b) Inoue, Y.; Takamuku, S.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1977, 1635. (c) Dauben, W. G.; vanRiel, H. C. H. A.; Robbins, J. D.; Wagner, G. J. J. Am. Chem. Soc. 1979, 101, 6383, (d) Inoue, Y.; Matsumoto, N.; Hakushi, T.; Srinivasan, R. J. Org. Chem. 1981, 46, 2267. (e) Saltiel, J.; Marchand, G. R.; Bonneau, R. J. Photochem. 1985, 28, 367. (f) Goodman, J. L.; Peters, K. S.; Misawa, H.; Caldwell, R. A. J. Am. Chem. Soc. 1986, 108, 6803. (g) Strickland, A. D.; Caldwell, R. A. J. Phys. Chem. 1993, 97, 13394.
34. Theoretical studies: (a) Verbeek, J.; van Lenthe, J. H.; Timmermans, P. J. J. A.; Mackor, A.; Budzelaar, P. H. M. J. Org. Chem. 1987, 52, 2955. (b) Johnson, R. P.; Di Rico, K. J. J. Org. Chem. 1995, 60, 1074.
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47. For previous theoretical studies on this problem, see: (a) Dewar, M. J. S.; Kirschner, S. J. Chem. Soc., Chem. Commun. 1975, 463. (b) Dewar, M. J. S.; Kirschner, S.; Kollmar, H. W. J Am. Chem. Soc. 1974, 96, 7571. (c) Tsuda, M., Oikawa, S.; Kimura, K. Int. J. Quantum Chem. 1980, 18, 157. (d) Jodkowski, J. T.; Ratajczak, E.; Zurawski, B. Bull. Acad. Pol. Sci. Ser. Sci. Chim. 1980, 28, 569. See also ref 13.
48. For previous theoretical studies on this problem, see: (a) Dewar, M. J. S.; Kirschner, S. J. Chem. Soc., Chem. Commun. 1975, 463. (b) Dewar, M. J. S.; Kirschner, S.; Kollmar, H. W. J Am. Chem. Soc. 1974, 96, 7571. (c) Tsuda, M., Oikawa, S.; Kimura, K. Int. J. Quantum Chem. 1980, 18, 157. (d) Jodkowski, J. T.; Ratajczak, E.; Zurawski, B. Bull. Acad. Pol. Sci. Ser. Sci. Chim. 1980, 28, 569. See also ref 13.
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60. See for example: (a) Lemal, D. M.; Dunlap, L. H., Jr. J. Am. Chem, Soc. 1972, 94, 6562. (b) Oth, J. F. M. Recl. Trav. Chim. Pays-Bas 1968, 87, 1185. (c) Schafer, W.; Hellmann, H. Angew. Chem., Int. Ed Engl 1967, 6, 518.