First synthesis of exomethylene paracyclophanes and their structural properties

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 5042-5047

  Saito, Shinichi ^a,b   Tsuboya, Norie ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PARACYCLOPHANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; INFRARED SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0030833837     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970727e     Document Type: Article

References (24)

1. For a review, see Cyclophane Chemistry; Fögtle, J. P., Ed.; Wiley: Chichester, England, 1993.
2. [9]- and [10]Paracyclophane: Wiesner, K.; MacDonald, D. M.; Ingraham, R. B.; Kelly, R. B. Can. J. Res., Sect. B. 1950, 28, 561-566. Bartlett, M. F.; Figdor, S. K.; Wiesner, K. Can. J. Chem. 1952, 30, 291-294. Cram, D. J.; Daeniker, H. U. J. Am. Chem. Soc. 1954, 76, 2743-2752.
3. [9]- and [10]Paracyclophane: Wiesner, K.; MacDonald, D. M.; Ingraham, R. B.; Kelly, R. B. Can. J. Res., Sect. B. 1950, 28, 561-566. Bartlett, M. F.; Figdor, S. K.; Wiesner, K. Can. J. Chem. 1952, 30, 291-294. Cram, D. J.; Daeniker, H. U. J. Am. Chem. Soc. 1954, 76, 2743-2752.
4. [9]- and [10]Paracyclophane: Wiesner, K.; MacDonald, D. M.; Ingraham, R. B.; Kelly, R. B. Can. J. Res., Sect. B. 1950, 28, 561-566. Bartlett, M. F.; Figdor, S. K.; Wiesner, K. Can. J. Chem. 1952, 30, 291-294. Cram, D. J.; Daeniker, H. U. J. Am. Chem. Soc. 1954, 76, 2743-2752.
5. [8]Paracyelophanes: Cram, D. J.; Knox, G. R. J. Am. Chem. Soc. 1961, 83, 2204-2205.
6. [7]Paracyclophanes: (a) Allinger, N. L.; Walter, T. J. J. Am. Chem. Soc. 1972, 94, 9267-9268. (b) Wolf, A. D.; Kane, V. V.; Levin, R. H.; Jones, M., Jr. J. Am. Chem. Soc. 1973, 95, 1680-1681.
7. [7]Paracyclophanes: (a) Allinger, N. L.; Walter, T. J. J. Am. Chem. Soc. 1972, 94, 9267-9268. (b) Wolf, A. D.; Kane, V. V.; Levin, R. H.; Jones, M., Jr. J. Am. Chem. Soc. 1973, 95, 1680-1681.
8. [6]Paracyciophane: Kane, V. V.; Wolf, A. D.; Jones, M., Jr. J. Am. Chem. Soc. 1974, 96, 2643-2644.
9. [5]Paracyclophane: Jenneskens, L. W.; de Kanter, F. J. J.; Kraakman, P. A.; Turkenburg, L. A. M.; Koolhaas, W. E.; de Wolf, W. H.; Bickelhaupt, F.; Tobe, Y.; Kakiuchi, K.; Odaira, Y. J. Am. Chem. Soc. 1985, 107, 3716-3717.
10. (a) Huisgen, V. R.; Rapp, W.; Ugi, I.; Walz, H.; Glogger, I. Justus Liebigs Ann. Chem. 1952, 586, 52-69.
11. (b) Kaneda, T.; Otsubo, T.; Horita, H.; Misumi. S. Bull. Chem. Soc. Jpn. 1980, 53, 1015-1018.
12. (c) Matsuoka, T.; Negi, T.; Otsubo, T.; Sakata, Y.; Misumi. S. Bull. Chem. Soc. Jpn. 1972, 45, 1825-1833.
13. (d) Tobe, Y.; Ueda, K.; Kakiuchi, K.; Odaira, Y. Chem. Lett. 1983, 1645-1646.
14. (e) Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 4895-4898.
15. (f) Han, N.; Lei, X.; Turro, N. J. J. Org. Chem. 1991, 56, 2927-2930.
16. Kane, V. V.: De Wolf, W. H.; Bickelhaupt, F. Tetrahedron 1994, 50, 4575-4622.
17. Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970-3971.
18. Klusener, P. A. A.; Kulik, W.; Brandsma, L. J. Org. Chem 1987, 52, 5261-5266.
19. This condition was originally used for the intermolecular cyclodimerization of conjugated enynes. See ref 9.
20. A modified procedure slightly improved the yield of 1g. Gevorgyan, V.; Tsuboya, N.; Saito, S.; Yamamoto, Y. Unpublished results.
21. Han, H.; Lei, X.; Turro, N. J. J. Org. Chem. 1991, 56, 2927-2930.
22. This result is in accordance with the data of [n]paracyelophanes reported by Misumi et al. See ref 7c.
23. Allinger et al. reported the bathochromic effect, which is caused by the deformation of the benzene ring, in the UV-vis spectra of [n]-paracyclophanes as the size of the ring becomes smaller. See, Allinger, N. L.; Freiberg, L, A.; Hermann, R. B.; Miller, M. A. J. Am. Chem. Soc. 1963, 85, 1171-1177.
24. Palladium Reagents in Organic Synthesis; Heck, R. F., Ed.; Acadimic Press: London, 1985.