A new one-pot synthesis of double-armed ionizable crown ethers using the mannich reaction

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5684-5685

  Chi, Ki Whan ^a,b   Wei, Han Chao ^a   Kottke, Thomas ^a   Lagow, Richard J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b University of Ulsan   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001146132     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960332f     Document Type: Article

References (19)

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2. (a) Lindoy, L. F. The Chemistry of Macrocyclic Ligand Complexes; Cambridge University: Cambridge, UK, 1989; p 116.
3. (b) Hiraoka, M. Crown Ethers and Analogous Compounds; Elsevier: Amsterdam, 1992; pp 126-128.
4. Nishida, H.; Tazaki, M.; Takagi, M.; Ueno, K. Mikrochim. Acta 1981, 281.
5. (a) Gustowski, D. A.; Gatto, V. J.; Mallen, J.; Echegoyen, L.; Gokel, G. W. J. Org. Chem. 1987, 52, 5172.
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9. (e) Tsukube, H.; Uenishi, J.; Higaki, H.; Kikkawa, K.; Tanaka, T.; Wakabayashi, S.; Oae, S. J. Org. Chem. 1993, 58, 4389.
10. (a) Lukyanenko, N. G.; Pastushok, V. N.; Bordunov, A. V. Synthesis 1991, 241.
11. (b) Lukyanenko, N. G.; Pastushok, V. N.; Bordunov, A. V.; Vetrogon, V. I.; Vetrogon, N. I.; Bradshaw, J. S. J. Chem. Soc., Perkin Trans. 1 1994, 1489.
12. (c) Bordunov, A. V.; Hellier, P. C.; Bradshaw, J. S.; Dalley, N. K.; Kou, X.; Zhang, X. X.; Izatt, R. M. J. Org. Chem. 1995, 60, 6097.
13. (d) Bordunov, A. V.; Lukyanenko, N. G.; Pastushok, V. N.; Krakowiak, K. E.; Bradshaw, J. S.; Dalley, N. K.; Kou, X. J. Org. Chem. 1995, 60, 4912.
14. (e) Zhang, X. X.; Bordunov, A. V.; Bradshaw, J. S.; Dalley, N. K.; Kou, X.; Izatt, R. M. J. Am. Chem. Soc. 1995, 117, 11507.
15. (a) Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46, 1791.
16. (b) Tramontini, M.; Angiolini, L. Mannich Base: Chemistry and Uses; CRC Press: Boca Raton, FL, 1994; pp 17-20.
17. The author has deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
18. Fronczek, F. R.; Gatto, V. J.; Minganti, C.; Schultz, R. A.; Gandour, R. D.; Gokel, G. W. J. Am. Chem. Soc. 1984, 106, 7244.
19. Silica gel (230-400 mesh) was deactivated by ∼2% triethylamine in eluent solution (40-70% of ethyl acetate in hexane).