Synthesis and structure of novel [2.n](4,4')binaphthylophanes: A new family in cyclophane chemistry

Tetrahedron Letters

Volumn 40, Issue 35, 1999, Pages 6435-6438

  Hayashida, Yoshitou ^a   Nakamura, Yosuke ^a   Chida, Yasushi ^a   Nishimura, Jun ^a  

^a GUNMA UNIVERSITY   (Japan)

Author keywords

Conformation; Cycloadditions; Cyclophanes; X ray crystal structures

Indexed keywords

(4,4')BINAPHTHYLOPHANE; CARBON; HYDROGEN; NAPHTHYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CRYSTAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033609866     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01232-0     Document Type: Article

References (20)

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10. Nishimura, J.; Okada, Y.; Inokuma, S.; Nakamura, Y.; Gao, S.-R. Synlett 1994, 884 and references cited therein.
11. The calculated distance between the two methyl carbons of cis-1,2-bis(4′-methyl-1,1′-binaphthyl-4-yl)cyclobutane is 6.77 Å. The distances between the terminal carbons for the most relaxed structures of pentane, hexane, and heptane are 5.09, 6.42, and 7.64 Å, respectively.
12. Nishimura, J.; Yamada, N.; Horiuchi, Y.; Ueda, E.; Ohbayashi, A.; Oku, A. Bull. Chem. Soc. Jpn. 1986, 59, 2035.
13. Mayer, F.; Sieglitz, A. Ber. 1922, 55, 1835.
14. Tamao, K.; Sumitani, K.; Kiso, Y; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
15. Rieche, A.; Gross, H.; Höft, E. Chem. Ber. 1960, 93, 88.
16. Wittig, G.; Geissler, G. Ann. 1953, 580, 44.
17. 3) δ 136.74, 136.73, 136.51, 135.67, 132.96, 132.47, 132.06, 131.86, 128.44, 127.37, 126.38, 126.28, 125.30, 125.24, 125.14, 124.49, 123.91, 123.80, 123.79, 123.00, 41.26, 30.67, 27.94, 27.37, 26.95, 22.01. HRMS calcd 656.3443, found 656.3442.
18. -1. Of total 5812 collected reflections, 3653 were observed. The final R (Rw) values were 0.061 (0.039).
19. Kress, R. B.; Duesler, E. N.; Etter, M. C.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1980, 102, 7709.
20. For the naphthalene moieties of the lower-pair of 5b, the distances between the two 1- and 4-carbons are 4.77 and 5.28 Å, respectively. Both are long enough for the inside pendulous motion. In fact, [3.3]naphthalenophane having 2.98 Å for the corresponding distance cannot transform its conformation from a syn- to an anti-one, whereas [3.4]naphthalenophane having 3.00 and 3.51 Å can do so, see: Nishimura, J.; Takeuchi, M.; Koike, M.; Sakamura, H.; Yamashita, O.; Okada, J.; Takaishi, N. Bull. Chem. Soc. Jpn. 1993, 66, 598.