Structures of bridged calix[6]arenes bearing a bromide functionality in the cavity

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 4039-4042

  Saiki, Toshiyuki ^b   Goto, Kei ^b   Tokitoh, Norihiro ^b   Goto, Midori ^a   Okazaki, Renji ^b  

^a NATL INST OF MAT AND CHEM RES   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARENE;

CALIXARENE; ORGANOBROMINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE;

EID: 0029927162     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00756-3     Document Type: Article

References (15)

1. (a) Gutsche, C. D. Calixarenes; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1989.
2. (b) Vicens, J., Böhmer, V., Eds. Calixarenes: A Versatile Class of Macrocyclic Compounds; Kluwer Academic Publishers: Dordrecht, 1991.
3. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
4. Tokitoh, N.; Saiki, T.; Okazaki, R. J. Chem. Soc., Chem. Commun. 1995, 1899-1900.
5. Saiki, T.; Goto, K.; Tokitoh, N.; Okazaki, R. J. Org. Chem. in press.
6. Ross, H.; Lüning, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 2555-2557.
7. (a) Kanamathareddy, S.; Gutsche, C. D. J. Am. Chem. Soc. 1993, 115, 6572-6579.
8. (b) Otsuka, H.; Araki, K.; Matsumoto, H.; Harada, T.; Shinkai, S. J. Org. Chem. 1995, 60, 4862-4867.
9. A part of this work has been presented in the 2nd Workshop on Calixarenes and Related Compounds, Kurume, Japan, June 2-4, 1993, PS/A-18.
10. Newcomb, M.; Moore, S. S.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6405.
11. A 10000-step Monte Carlo multiple-minimum conformational search was performed with MacroModel V4.5 program: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
12. Andreetti, G. D.; Calestani, G.; Ugozzoli, F.; Arduini, A.; Ghidini, E.; Pochini, A.; Ungaro, R. J. Inclusion Phenom. 1987, 5, 123-126.
13. Harada, T.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 1995, 2231-2242.
14. -1. The intensity data were collected on an Enraf-Nonius CAD-4 diffractometer with CuKα radiation λ = 1.5418 Å), and the structure was solved by direct methods (MULTAN 78) using a program system UNICS III. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included but not refined. The final cycle of full-matrix least-squares refinement was based on 4692 observed reflections [I > 3.00σ(I)] and 478 variable parameters with R (Rw) = 0.079 (0.091). Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.
15. For the conformational notations, see ref 5a.