Synthesis and unusual crystal structure of syn-6,15-dicyano-2,11-dithia[3.3]metacyclophane

Tetrahedron Letters

Volumn 38, Issue 43, 1997, Pages 7475-7478

  Bodwell, Graham J ^a   Bridson, John N ^a   Houghton, Tom J ^a   Yarlagadda, Bala ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON;

ARTICLE; CALCULATION; CRYSTAL STRUCTURE; DIPOLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM CHEMISTRY; SOLID STATE; STEREOCHEMISTRY;

EID: 0030824830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01794-2     Document Type: Article

References (18)

1. a) Cyclophanes, Vols. 1 and 2, (Eds.: Keehn, P.M., Rosenfeld, S.M.), Academic Press, New York, 1983;
2. b) Vögtle, F. Cyclophan-Chemie, B.G. Teubner, Stuttgart, 1990;
3. c) Diederich, F.N. Cyclophanes, Royal Society of Chemistry, London, 1991.
4. Bodwell, G.J., Houghton, T.J., Kennedy, J.W.J., Mannion, M.R. Angew. Chem. 1996, 108, 2280-2281; Angew. Chem. Int. Ed. Engl. 1996, 35, 2121-2123.
5. Bodwell, G.J., Houghton, T.J., Kennedy, J.W.J., Mannion, M.R. Angew. Chem. 1996, 108, 2280-2281; Angew. Chem. Int. Ed. Engl. 1996, 35, 2121-2123.
6. Bodwell, G.J., Bridson, J.N., Houghton, T.J., Kennedy, J.W.J., Mannion, M.R. Angew. Chem. 1996, 108, 1418-1420; Angew. Chem. Int. Ed. Engl. 1996, 35, 1320-1321.
7. Bodwell, G.J., Bridson, J.N., Houghton, T.J., Kennedy, J.W.J., Mannion, M.R. Angew. Chem. 1996, 108, 1418-1420; Angew. Chem. Int. Ed. Engl. 1996, 35, 1320-1321.
8. 3) δ = 138.6, 135.2, 130.7, 117.9, 112.8, 37.6; LRMS (EI, 70 eV), m/z (%) 323 (24), 322 (100, M+), 221 (7), 192 (23), 163 (13), 162 (86), 161 (84), 160 (32), 131 (69), 130 (99), 129 (26), 116 (23), 103 (23); HRMS calcd. 322.0598, found 322.0591.
9. Bodwell, G.J., Houghton, T.J., Koury, H.E., Yarlagadda, B. Synlett 1995, 751-752.
10. Mitchell, R.H. in reference 1a, Vol. 1, p. 239-310.
11. w = 0.039, GOF = 1.73.
12. Mitchell R.H., Anker W., Bushnell G.W. Can. J. Chem. 57:1979;3080-3087.
13. This numbering is the crystallographic numbering, which differs from the systematic numbering.
14. Pauling, L. The Nature of the Chemical Bond, 3rd ed., Cornell University, Ithaca, 1960.
15. Newkome G.R., Pappalardo S., Fronczek F.R. J. Am. Chem. Soc. 105:1983;5152-5153.
16. Sako, K., Tatemitsu, H., Onaka, S., Takemura, H., Osada, S., Wen, G., Rudzinski, J.M., Shinmyozu, T. Liebigs Ann. 1996, 1645-1649.
17. Sako, K., Hirakawa, T., Fujimoto, N., Shinmyozu, T., Inazu, T., Horimoto, H. Tetrahedron Lett. Chem. 1992, 57, 6536-6541; Semmelhack, M.F., Harrison, J.J., Young, D.C., Gutiérrez, A., Rafii, A.S., Clardy, J. J. Am. Chem. Soc. 1989, 107, 7508-7514.
18. Sako, K., Hirakawa, T., Fujimoto, N., Shinmyozu, T., Inazu, T., Horimoto, H. Tetrahedron Lett. Chem. 1992, 57, 6536-6541; Semmelhack, M.F., Harrison, J.J., Young, D.C., Gutiérrez, A., Rafii, A.S., Clardy, J. J. Am. Chem. Soc. 1989, 107, 7508-7514.