Plyers-shaped diamines I. 3-endo-Amino-2,4-cyclotropane-and 3-endo- amino-2,4-cyclogranatanecarbonitriles

Tetrahedron

Volumn 54, Issue 26, 1998, Pages 7401-7416

  Vilsmaier, Elmar ^a   Herweck, Thomas ^a   Schummel, Monika ^a   Tetzlaff, Claus ^a   Dotzauer, Matthias ^a   Bergsträßer, Uwe ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Configuration; Conformation; Diamines; Polycyclic heterocyclic compounds

Indexed keywords

3 AMINO 2,4 CYCLOGRANATANECARBONITRILE; 3 AMINO 2,4 CYCLOTROPANE; TROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032565910     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00382-2     Document Type: Article

References (43)

1. [1] Tetzlaff C, Butz V, Vilsmaier E, Wagemann R, Maas G, Ritter v Onciul A, Clark T. J. Chem. Soc. Perkin Trans. 2 1993:1901-1905.
2. [2] Schlag W-R, Vilsmaier E, Maas G. Tetrahedron 1994;50:3123-3138.
3. [3] Seibel J, Vilsmaier E, Fröhlich K, Maas G, Wagemann R. Tetrahedron 1994;50:715-730.
4. [4] Wagemann R, Vilsmaier E, Maas G. Tetrahedron 1995;51:8815-8828.
5. [5] Butz V, Vilsmaier E, Maas G. J. Chem. Soc. Perkin Trans. 2 1993:1907-1913.
6. [6] Vilsmaier E, Milch G, Fröhlich K, Bergsträßer U, Ritter v Onciul A, Clark T. Tetrahedron 1995;51:3507-3520.
7. [7] Butz V, Vilsmaier E. Tetrahedron 1993;49:6031-6044.
8. [8] Tetzlaff C, Vilsmaier E, Schlag W-R. Tetrahedron 1990;46:8117-8130.
9. [9] Vilsmaier E, Tetzlaff C, Butz V, Maas G. Tetrahedron 1991;47:8133-8144.
10. [10] Vilsmaier E, Grosse M, Schlag W-R, Milch G, Bergsträßer U. J. prakt. Chem. 1996;338:479-484.
11. [11] Vilsmaier E, Dotzauer M, Wagemann R, Tetzlaff C, Fath J, Schlag W-R, Bergsträßer U. Tetrahedron 1995;51:11183-11198.
12. [12] Dotzauer M, Eisfeld W, Vilsmaier E, Fröhlich K, Bergsträßer U, Tetzlaff C. J. Org. Chem. 1996;61:8526-8532.
13. [13] White WA, Weingarten H. J. Org. Chem. 1967;32:213-218.
14. [14] Schwarzenbach G. Helv. Chim. Acta 1950;33:947-962.
15. [15] Prinzbach H, Eberbach W, Klaus M, von Veh G. Chem. Ber. 1968;101.4066-4082.
16. [16] Saito K, Ito K, Takahashi K. Heterocycles 1989;29:2135-2140.
17. [17] Baird MS. J. Chem. Soc. Perkin Trans. 1 1979:1020-1028.
18. [18] Vilsmaier E, Stamm T, Dauth W, Tetzlaff C, Barth S. Bull. Soc. Chim. Belg. 1992;100:37-44.
19. [19] Vilsmaier E, Tröger W. Angew. Chem. Int. Ed. Engl. 1979;18:798; Vilsmaier E, Tröger W, Haag G. Chem. Ber. 1981;114:67-79.
20. [19] Vilsmaier E, Tröger W. Angew. Chem. Int. Ed. Engl. 1979;18:798; Vilsmaier E, Tröger W, Haag G. Chem. Ber. 1981;114:67-79.
21. [20] Vilsmaier E. Bull. Soc. Chim. Belg. 1985;94:521-554.
22. [21] Vilsmaier E, Adam R, Tetzlaff C, Cronauer R. Tetrahedron 1989;45:3683-3694.
23. [22] Vilsmaier E, Schwaben B, Joerg K. Chem. Ber. 1984;117:2900-2909.
24. [23] Günther H. NMR-Spektroskopie, Stuttgart: G. Thieme, 1983:229-23.
25. [24] Fernández MJ, Huertas R, Gàlvez E. J. Mol. Struct. 1991;246:359-366; Fernàndez MJ, Huertas R, Gálvez E, Sanz-Aparicio J, Fonseca I. J. Mol. Struct. 1992;266:283-288.
26. [24] Fernández MJ, Huertas R, Gàlvez E. J. Mol. Struct. 1991;246:359-366; Fernàndez MJ, Huertas R, Gálvez E, Sanz-Aparicio J, Fonseca I. J. Mol. Struct. 1992;266:283-288.
27. [25] Fernández MJ, Huertas RM, Gàlvez E, Orjales A, Berisa A, Labeaga L, Gago F, Fonseca I, Sanz-Aparicio J, Cano FH, Albert A, Fayos J. J. Chem. Soc. Perkin Trans. 2 1992:687-695.
28. [26] Calm MP Resonans, Version 2.0, Heratonic Programs, Moscow 1991.
29. [27] SHELXTL-Plus Release 4.2 Siemens Analytical X-ray Instruments 1991.
30. [28] Gàlvez E, Arias MS, Cabezas N, Martinez M. J. Mol. Struct. 1990;220:55-61.
31. [29] Burgos C, Izquierdo ML, Arias MS, Gàlvez E, Sanz-Aparicio J, Fonseca I, Bellanato J. J. Mol. Struct. 1992;267:79-86.
32. [30] Burgos C, Gàlvez E, Izquierdo ML, Arias MS, Matesanz E, Martinez-Ripoll M, Bellanato J. J. Mol. Struct. 1992;269:123-139.
33. [31] Izquierdo ML, Gàlvez E, Burgos C, Arias MS, Sanz-Aparicio J, Fonseca I, Bellanato J. J. Mol. Struct. 1993;291:1-10.
34. [32] Llamas-Saiz AL, Foces-Foces C, Elguero J. J. Mol. Struct. 1994;328:297-323.
35. [33] Wong-Ng W, Nyburg SC, Awwal A, Jankie R, Kresge AJ. Acta Cryst. 1982;B38:559-564.
36. [34] Boczon W. Heterocycles 1992;33:1101-1128.
37. [35] Przybylska M, Barnes WH. Acta Cryst. 1953;6:377-384.
38. [36] Trefonas LM, Cheung LD, Majeste RJ, Brown JN. Cryst. Struct. Comm. 1977;6:307.
39. [37] Kunze UR. Grundlagen der quantitativen Analyse, Stuttgart: G Thieme, 1980:80-81.
40. [38] Boehringer & Soehne, NL-Pat 285 470, Chem. Abstr. 1965;63:4354 d.
41. [39] Atomic co-ordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield, Cambridge, CB2 1EW. The X-ray data are available on request from the Director of the CCDC by quoting the full literature citation of this paper.
42. [40] Sheldrick GM. SHELXS-86, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1986.
43. [41] Sheldrick GM. SHELXL-93, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1993.