Unusual [16] and [18]Metaheterophanes with a Quadrupolar Character

Synlett

Volumn 1996, Issue 3, 1996, Pages 285-288

  Alcalde, Ermitas ^a   Gisbert, Maria ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002614023     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5384     Document Type: Article

References (16)

1. (a) Diederich, F. In Cyclophanes, vol. 2 in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1991.
2. (b) Vögtle, F. Cyclophane Chemistry, Wiley, Chichester, 1993.
3. (a) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens J.; Böhmer, V.; Eds.; Kluwer: Dordrecht, 1991.
4. (b) Gutsche, C. D. In Calixarenes, vol. 1 in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1989.
5. (c) Shinkai, S. Tetrahedron, 1993, 49, 8933.
6. 4]heterophane 1 has been secured by X-ray crystallographic diffraction. 4
7. Alcalde, E.; Alemany, M.; Gisbert, M.; Pérez-García, L. Synlett 1995, 757 and references cited therein.
8. Bradshaw, J.S.; Nielsen, R.B.; Tse, P.-K.; Arena, G.; Wilson, B.E.; Dalley, N.K.; Lamb, J.D.; Christensen, J.J.; Izatt, R.M. J. Heterocyclic Chem. 1986, 23, 361.
9. Lee, W.Y.; Park, C.H.; Kim, Y.D. J. Org. Chem. 1992, 57, 4074.
10. (a) Tarrago, G.; Marzin, C.; Najimi, O.; Pellegrin, V. J. Org. Chem. 1990, 55, 420, and references cited therein.
11. (b) Martínez-Díaz, M.V.; Mendoza, J.; Torres, T. Synthesis 1994, 1091, and references cited therein.
12. (c) Martínez-Díaz, M. V.; Mendoza, J.; Santos, F.; Torres, T. Tetrahedron Asymmetry 1994, 5, 1291.
13. 2-2,18,23,40), 124.1 (CH-21,22,43,44), 128.7 (CH-4,17,26, 39), 130.3 (CH-46,48,50,52), 130.9 (CH-5,6,15,16,27,28,37, 38), 135.7 (C-3,8,25,40), 137.6 (CH-45,49), 138.6 (C-7,14, 29,36), 159.2 (C-9,12,31,34).
14. Inspection of the CH protons for the benzene rings revealed that the lineshapes of the signals corresponded to the expected splitting patterns for bis-betaine 2 and macrocycle 7 at 500 MHz.
15. 2-2,19,24,41= -0.13 ppm. 11
16. 8]heterophanes 2 and 3 these signals (H-33,37 for 2 and H-45,49 for 3) were absent due to H-D exchange.