Stopping the aromatic ring current. Synthesis of the first bis-metal complexes benzannulene. On the way to a molecular conductor with a photo-switch

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6665-6668

  Mitchell, Reginald H ^a   Chen, Yongsheng ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030576960     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01491-8     Document Type: Article

References (29)

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2. 1. Haddon, R. C. Tetrahedron 1972, 28, 3635-3655; Mitchell, R. H. Adv. in Theoret. Interesting Molec. 1989, 1, 135-199.
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5. 3. Mitchell, R. H.; Iyer, V. S.; Khalifa, N.; Mahadevan, R.; Venugopalan, S.; Weerawarna, S. A.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 1514-1532.
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8. 5. See for example: Gompper, R.; Illek, C.; Polborn, K. Tetrahedron Lett. 1992, 33, 3989-3992; Giannini, L.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem. Int. Ed Engl. 1994, 33, 2204-2206.
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10. 6. Günther, H.; Grimme, W. Angew. Chem. Int. Ed. Engl. 1966, 5, 1043-1044; Stöckel, K.; Sondheimer, F.; Clarke, T. A.; Guss, J. M.; Mason, R. J. Am. Chem. Soc. 1971, 93, 2571-2572; GUss, J. M.; Mason, R. J. C. S. Dalton, 1973, 1834-1840; Hilken, G.; Kinkel, T.; Schwamborn, M.; Lex, J.; Schmickler, H.; Vogel, E. Angew. Chem. Int Ed. Engl. 1982, 21, 784; Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 4966-4968; Mitchell, R. H.; Zhou, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1013-1015.
11. 6. Günther, H.; Grimme, W. Angew. Chem. Int. Ed. Engl. 1966, 5, 1043-1044; Stöckel, K.; Sondheimer, F.; Clarke, T. A.; Guss, J. M.; Mason, R. J. Am. Chem. Soc. 1971, 93, 2571-2572; GUss, J. M.; Mason, R. J. C. S. Dalton, 1973, 1834-1840; Hilken, G.; Kinkel, T.; Schwamborn, M.; Lex, J.; Schmickler, H.; Vogel, E. Angew. Chem. Int Ed. Engl. 1982, 21, 784; Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 4966-4968; Mitchell, R. H.; Zhou, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1013-1015.
12. 6. Günther, H.; Grimme, W. Angew. Chem. Int. Ed. Engl. 1966, 5, 1043-1044; Stöckel, K.; Sondheimer, F.; Clarke, T. A.; Guss, J. M.; Mason, R. J. Am. Chem. Soc. 1971, 93, 2571-2572; GUss, J. M.; Mason, R. J. C. S. Dalton, 1973, 1834-1840; Hilken, G.; Kinkel, T.; Schwamborn, M.; Lex, J.; Schmickler, H.; Vogel, E. Angew. Chem. Int Ed. Engl. 1982, 21, 784; Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 4966-4968; Mitchell, R. H.; Zhou, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1013-1015.
13. 6. Günther, H.; Grimme, W. Angew. Chem. Int. Ed. Engl. 1966, 5, 1043-1044; Stöckel, K.; Sondheimer, F.; Clarke, T. A.; Guss, J. M.; Mason, R. J. Am. Chem. Soc. 1971, 93, 2571-2572; GUss, J. M.; Mason, R. J. C. S. Dalton, 1973, 1834-1840; Hilken, G.; Kinkel, T.; Schwamborn, M.; Lex, J.; Schmickler, H.; Vogel, E. Angew. Chem. Int Ed. Engl. 1982, 21, 784; Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 4966-4968; Mitchell, R. H.; Zhou, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1013-1015.
14. 6. Günther, H.; Grimme, W. Angew. Chem. Int. Ed. Engl. 1966, 5, 1043-1044; Stöckel, K.; Sondheimer, F.; Clarke, T. A.; Guss, J. M.; Mason, R. J. Am. Chem. Soc. 1971, 93, 2571-2572; GUss, J. M.; Mason, R. J. C. S. Dalton, 1973, 1834-1840; Hilken, G.; Kinkel, T.; Schwamborn, M.; Lex, J.; Schmickler, H.; Vogel, E. Angew. Chem. Int Ed. Engl. 1982, 21, 784; Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 4966-4968; Mitchell, R. H.; Zhou, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1013-1015.
15. 7. Neidlein, R.; Gürtler, S.; Krieger, C. Helv. Chim. Acta 1994, 77, 2303-2322; Solooki, D.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J. Organometallics, 1994, 13, 451-455; Solooki, D.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J.; See, R. F.; Churchill, M.; Ferrara, J. D. J. Orgmet. Chem. 1994, 470, 231-236.
16. 7. Neidlein, R.; Gürtler, S.; Krieger, C. Helv. Chim. Acta 1994, 77, 2303-2322; Solooki, D.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J. Organometallics, 1994, 13, 451-455; Solooki, D.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J.; See, R. F.; Churchill, M.; Ferrara, J. D. J. Orgmet. Chem. 1994, 470, 231-236.
17. 7. Neidlein, R.; Gürtler, S.; Krieger, C. Helv. Chim. Acta 1994, 77, 2303-2322; Solooki, D.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J. Organometallics, 1994, 13, 451-455; Solooki, D.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J.; See, R. F.; Churchill, M.; Ferrara, J. D. J. Orgmet. Chem. 1994, 470, 231-236.
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19. 9. See for example: Katz, T. J.; Ślusarek, W. J. Am. Chem. Soc. 1978, 101, 4259-4267; Katz, T. J.; Sudhakar, A.; Teasley, M. F.; Gilbert, A. M.; Geiger, W. E.; Robben, M. P.; Wuensch, M.; Ward, M. D. J. Am. Chem. Soc. 1993, 115, 3182-3198; Elschenbroich, Ch.; Heck, J. J. Am. Chem. Soc. 1979, 101, 6773-6776.
20. 9. See for example: Katz, T. J.; Ślusarek, W. J. Am. Chem. Soc. 1978, 101, 4259-4267; Katz, T. J.; Sudhakar, A.; Teasley, M. F.; Gilbert, A. M.; Geiger, W. E.; Robben, M. P.; Wuensch, M.; Ward, M. D. J. Am. Chem. Soc. 1993, 115, 3182-3198; Elschenbroich, Ch.; Heck, J. J. Am. Chem. Soc. 1979, 101, 6773-6776.
21. 9. See for example: Katz, T. J.; Ślusarek, W. J. Am. Chem. Soc. 1978, 101, 4259-4267; Katz, T. J.; Sudhakar, A.; Teasley, M. F.; Gilbert, A. M.; Geiger, W. E.; Robben, M. P.; Wuensch, M.; Ward, M. D. J. Am. Chem. Soc. 1993, 115, 3182-3198; Elschenbroich, Ch.; Heck, J. J. Am. Chem. Soc. 1979, 101, 6773-6776.
22. 10. Blattmann, H. R.; Meuche, D.; Heilbronner, E.; Molyneux, R. J.; Boekelheide, V. J. Am. Chem. Soc. 1965, 87, 130-131. Blattmann, H. R.; Schmidt, W. Tetrahedron 1970, 26, 5885-5899; Schmidt, W. Helv. Chim. Acta 1971, 54, 862-868; Schmidt, W. Tetrahedron Lett. 1972, 12, 581-584; Mitchell, R. H.; Iyer, V. S.; Mahadevan, R.; Venugopalan, S.; Zhou, P. J. Org. Chem. 1996, 61, in press.
23. 10. Blattmann, H. R.; Meuche, D.; Heilbronner, E.; Molyneux, R. J.; Boekelheide, V. J. Am. Chem. Soc. 1965, 87, 130-131. Blattmann, H. R.; Schmidt, W. Tetrahedron 1970, 26, 5885-5899; Schmidt, W. Helv. Chim. Acta 1971, 54, 862-868; Schmidt, W. Tetrahedron Lett. 1972, 12, 581-584; Mitchell, R. H.; Iyer, V. S.; Mahadevan, R.; Venugopalan, S.; Zhou, P. J. Org. Chem. 1996, 61, in press.
24. 10. Blattmann, H. R.; Meuche, D.; Heilbronner, E.; Molyneux, R. J.; Boekelheide, V. J. Am. Chem. Soc. 1965, 87, 130-131. Blattmann, H. R.; Schmidt, W. Tetrahedron 1970, 26, 5885-5899; Schmidt, W. Helv. Chim. Acta 1971, 54, 862-868; Schmidt, W. Tetrahedron Lett. 1972, 12, 581-584; Mitchell, R. H.; Iyer, V. S.; Mahadevan, R.; Venugopalan, S.; Zhou, P. J. Org. Chem. 1996, 61, in press.
25. 10. Blattmann, H. R.; Meuche, D.; Heilbronner, E.; Molyneux, R. J.; Boekelheide, V. J. Am. Chem. Soc. 1965, 87, 130-131. Blattmann, H. R.; Schmidt, W. Tetrahedron 1970, 26, 5885-5899; Schmidt, W. Helv. Chim. Acta 1971, 54, 862-868; Schmidt, W. Tetrahedron Lett. 1972, 12, 581-584; Mitchell, R. H.; Iyer, V. S.; Mahadevan, R.; Venugopalan, S.; Zhou, P. J. Org. Chem. 1996, 61, in press.
26. 10. Blattmann, H. R.; Meuche, D.; Heilbronner, E.; Molyneux, R. J.; Boekelheide, V. J. Am. Chem. Soc. 1965, 87, 130-131. Blattmann, H. R.; Schmidt, W. Tetrahedron 1970, 26, 5885-5899; Schmidt, W. Helv. Chim. Acta 1971, 54, 862-868; Schmidt, W. Tetrahedron Lett. 1972, 12, 581-584; Mitchell, R. H.; Iyer, V. S.; Mahadevan, R.; Venugopalan, S.; Zhou, P. J. Org. Chem. 1996, 61, in press.
27. 3; see Peitz, D. J.; Palmer, R. T.; Radonovich, L. J.; Woolsey, N. F. Organometallics, 1993, 12, 4580-4584. Corresponding spectral properties.
28. max) nm 218 (52,000), 336 (31,100), 438 (20,300).
29. 3 group causes an analogous 0.11 ppm deshielding on the less affected methyl group, the ring current in 5 might be 2% higher. We believe the RCS is too large for the RC to be 0%.