The proton cryptate of hexaethylenetetramine

Angewandte Chemie - International Edition

Volumn 38, Issue 7, 1999, Pages 956-959

  Miyahara, Yuji ^a   Tanaka, Yurika ^a   Amimoto, Kiichi ^a   Akazawa, Takamitsu ^a   Sakuragi, Tsutomu ^a   Kobayashi, Haruhito ^a   Kubota, Kazuomi ^a   Suenaga, Masahiko ^a   Koyama, Hiroyuki ^a   Inazu, Takahiko ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Cage compounds; Cryptates; Nitrogen heterocycles

Indexed keywords

ETHYLENE DERIVATIVE; HEXAETHYLENETETRAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CRYSTALLIZATION; ENANTIOMER; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0033118621     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990401)38:7<956::AID-ANIE956>3.0.CO;2-K     Document Type: Article

References (14)

1. h) has now been realized in the structure of dodecahedrane: a) R. J. Ternansky, D. W. Balough, L. A. Paquette, J. Am. Chem. Soc. 1982, 104, 4503-4504;
2. b) L. A. Paquette, Proc. Natl. Acad. Sci. USA 1982, 79, 4495-4500;
3. c) L. A. Paquette, Y. Miyahara, C. W. Doecke, J. Am. Chem. Soc. 1986, 108, 1716-1718.
4. H. Koyama, T. Yoshino, Bull. Chem. Soc. Jpn. 1972, 45, 481-484.
5. +@1 at the center of the cavity: S. T. Howard, I. A. Fallis, J. Org. Chem. 1998, 49, 7117-7119.
6. H. Takemura, T. Shinmyozu, T. Inazu, J. Am. Chem. Soc. 1991, 113, 1323-1331.
7. J. Springborg, C. E. Olsen, I. Søtofte, Acta Chem. Scand. 1995, 49, 555-563.
8. The tetramine 5 (l = m = n = o = p = q = 3) has also been reported: a) J. Springborg, U. Pretzmann, C. E. Olsen, Acta Chem. Scand. 1996, 50, 294-298;
9. b) J. Springborg, U. Pretzmann, C. E. Olsen, I. Søtofte, Acta Chem. Scand. 1998, 52, 289-296.
10. Springborg et al. mentioned their failure to obtain 10 by their approach: J. Springborg, P. Kofod, C. E. Olsen, I. Søtofte, Acta Chem. Scand. 1995, 49, 564-570.
11. J. L. Sessler, J. W. Sibert, V. Lynch, Inorg. Chem. 1990, 29, 4143-4146.
12. The yield of 8 increased as the boiling temperature of the solvent was raised on going from benzene to toluene to xylene. In addition, when one of the ethylene bridges in 7 was replaced by a less sterically demanding o-phenylene bridge, the cyclization occurred readily at room temperature in 53% yield: Y. Miyahara, K. Handou, T. Inazu, unpublished results.
13. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-103234. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
14. Review: R. W. Alder, Tetrahedron 1990, 46, 683-713.