New 'proton sponges', 13[≠] syntheses, structures and basicities of 1,2,4,5-tetrakis(dimethylamino)benzene and 2,3,6,7- tetrakis(dimethylamino)naphthalene

European Journal of Organic Chemistry

Volumn , Issue 2, 2000, Pages 327-333

  Staab, Heinz A ^a   Elbl Weiser, Karin ^a   Krieger, Claus ^a  

^a MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

Author keywords

'Proton sponge' analogues; Crystal structures; Cyanine structures versus aromaticity in benzene dications; Orientation dependence of hydrogen bonds

Indexed keywords

BENZENE DERIVATIVE; NAPHTHALENE DERIVATIVE;

ALKALINITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGEN BOND; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033972181     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200001)2000:2<327::aid-ejoc327>3.0.co;2-z     Document Type: Article

References (19)

1. R. W. Alder, P. S. Bowman, W. R. S. Steele, D. R. Winterman, J. Chem. Sac., Chem. Commun. 1968, 723; R. W. Alder, N. C. Goode, N. Miller, F. Hibbert, K. P. P. Hunte, H. J. Robbins, J. Chem. Soc., Chem. Commun. 1978, 89.
2. R. W. Alder, P. S. Bowman, W. R. S. Steele, D. R. Winterman, J. Chem. Sac., Chem. Commun. 1968, 723; R. W. Alder, N. C. Goode, N. Miller, F. Hibbert, K. P. P. Hunte, H. J. Robbins, J. Chem. Soc., Chem. Commun. 1978, 89.
3. F. Hibbert, J. Chem. Soc., Perkin Trans. 2 1974, 1862; F. Hibbert, K. P. P. Hunte, J. Chem. Soc., Perkin Trans. 2 1983, 1895; further references therein.
4. F. Hibbert, J. Chem. Soc., Perkin Trans. 2 1974, 1862; F. Hibbert, K. P. P. Hunte, J. Chem. Soc., Perkin Trans. 2 1983, 1895; further references therein.
5. Review on "proton sponges": H. A. Staab, T. Saupe, Angew. Chem. 1988, 100, 895-909; Angew. Chem. Int. Ed. Engl. 1988, 27, 865-878.
6. Review on "proton sponges": H. A. Staab, T. Saupe, Angew. Chem. 1988, 100, 895-909; Angew. Chem. Int. Ed. Engl. 1988, 27, 865-878.
7. R. C. Weast (Ed.), Handbook of Chemistry and Physics, 68th ed., CRC Press, Inc., Boca Raton, Florida, 1968, section D, pp. 159-162.
8. Short communication: K. Elbl, C. Krieger, H. A. Staab. Angew. Chem. 1986, 98, 1024-1026; Angew. Chem. Int. Ed. Engl. 1986, 25, 1023-1024; H. A. Staab, K. Elbl, C. Krieger, Tetrahedron Lett. 1986, 27, 5719-5722; K. Elbl-Weiser, C. Krieger, H. A. Staab, Angew. Chem. 1990, 102, 183-185; Angew. Chem. Int. Ed. Engl. 1990, 29, 211-213.
9. Short communication: K. Elbl, C. Krieger, H. A. Staab. Angew. Chem. 1986, 98, 1024-1026; Angew. Chem. Int. Ed. Engl. 1986, 25, 1023-1024; H. A. Staab, K. Elbl, C. Krieger, Tetrahedron Lett. 1986, 27, 5719-5722; K. Elbl-Weiser, C. Krieger, H. A. Staab, Angew. Chem. 1990, 102, 183-185; Angew. Chem. Int. Ed. Engl. 1990, 29, 211-213.
10. Short communication: K. Elbl, C. Krieger, H. A. Staab. Angew. Chem. 1986, 98, 1024-1026; Angew. Chem. Int. Ed. Engl. 1986, 25, 1023-1024; H. A. Staab, K. Elbl, C. Krieger, Tetrahedron Lett. 1986, 27, 5719-5722; K. Elbl-Weiser, C. Krieger, H. A. Staab, Angew. Chem. 1990, 102, 183-185; Angew. Chem. Int. Ed. Engl. 1990, 29, 211-213.
11. Short communication: K. Elbl, C. Krieger, H. A. Staab. Angew. Chem. 1986, 98, 1024-1026; Angew. Chem. Int. Ed. Engl. 1986, 25, 1023-1024; H. A. Staab, K. Elbl, C. Krieger, Tetrahedron Lett. 1986, 27, 5719-5722; K. Elbl-Weiser, C. Krieger, H. A. Staab, Angew. Chem. 1990, 102, 183-185; Angew. Chem. Int. Ed. Engl. 1990, 29, 211-213.
12. Short communication: K. Elbl, C. Krieger, H. A. Staab. Angew. Chem. 1986, 98, 1024-1026; Angew. Chem. Int. Ed. Engl. 1986, 25, 1023-1024; H. A. Staab, K. Elbl, C. Krieger, Tetrahedron Lett. 1986, 27, 5719-5722; K. Elbl-Weiser, C. Krieger, H. A. Staab, Angew. Chem. 1990, 102, 183-185; Angew. Chem. Int. Ed. Engl. 1990, 29, 211-213.
13. R. Nietzki, E. Hagenbach, Ber. Dtsch. Chem. Ges. 1887, 20. 328; R. Nietzki, Ber. Dtsch. Chem. Ges. 1887, 20, 2114.
14. R. Nietzki, E. Hagenbach, Ber. Dtsch. Chem. Ges. 1887, 20. 328; R. Nietzki, Ber. Dtsch. Chem. Ges. 1887, 20, 2114.
15. P. Ruggli, R. Fischer, Helv. Chim. Acta 1945, 28, 1270.
16. R. F. Borch, A. I. Hassid, J. Org. Chem. 1972, 37, 1673.
17. Preliminary communication: T. Barth, C. Krieger, F. A. Neugebauer, H. A. Staab, Angew. Chem. 1991, 103, 1006-1008; Angew. Chem. Int. Ed. Engl. 1991, 30, 1028-1030; J. Chem. Soc., Chem. Commun. 1993, 14, 1129-1131.
18. Preliminary communication: T. Barth, C. Krieger, F. A. Neugebauer, H. A. Staab, Angew. Chem. 1991, 103, 1006-1008; Angew. Chem. Int. Ed. Engl. 1991, 30, 1028-1030; J. Chem. Soc., Chem. Commun. 1993, 14, 1129-1131.
19. Preliminary communication: T. Barth, C. Krieger, F. A. Neugebauer, H. A. Staab, Angew. Chem. 1991, 103, 1006-1008; Angew. Chem. Int. Ed. Engl. 1991, 30, 1028-1030; J. Chem. Soc., Chem. Commun. 1993, 14, 1129-1131.