2,3-Dialkynyl-1,4-diazabuta-1,3-dienes as novel π-systems: Synthesis, structure, and electronic properties

European Journal of Organic Chemistry

Volumn , Issue 1, 1999, Pages 205-214

  Faust, Rüdiger ^a,b   Göbelt, Bernd ^a,b   Weber, Christian ^a,b   Krieger, Claus ^c   Gross, Maurice ^d   Gisselbrecht, Jean Paul ^d   Boudon, Corinne ^d  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

^d CNRS   (France)

Author keywords

Alkynes; Cyclic voltammetry; Diazabutadienes; Electronic structure; UV Vis spectroscopy

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ALKYNYL GROUP;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; OXIDATION REDUCTION POTENTIAL; POTENTIOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0344117813     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199901)1999:1<205::AID-EJOC205>3.0.CO;2-Q     Document Type: Article

References (73)

1. [1a] K. N. Mehrotra, G. Singh, Synthesis 1980, 1001-1004.
2. [1b] M. Zettlitzer, H. tom Dieck, E. T. K. Haupt, L. Stamp, Chem. Ber. 1986, 119, 1868-1875.
3. [1c] H. tom Dieck, M. Zettlitzer, Chem. Ber. 1987, 120, 795-801.
4. [1d] M. Takahashi. H. Miyahara, N. Yoshida, Heterocycles 1988, 27, 155-160.
5. [1e] H. tom Dieck, U. Verfürth, K. Diblitz, J. Ehlers, G. Fendesack, Chem. Ber. 1989, 122, 129-131.
6. [1f] B. Alcaide, A. Gomez, J. Plumet, J. Rodriguez-Lopez, Tetrahedron 1989, 45, 2751-2762.
7. [1g] K. Bootz, W. P. Neumann, Tetrahedron Lett. 1989, 30, 6669-6672.
8. [1h]J. Heinicke, B. Gehrhus, J. Organomet. Chem. 1992, 423, 13-21.
9. [1i] J. Alcázar, M. Begtrup, A. de la Hoz, J. Chem. Soc., Perkin Trans. 1 1995, 2467-2470.
10. [1j] J. Alcázar, M. Begtrup, A. de la Hoz, Heterocycles 1996, 43, 1465-1470.
11. [1k] J. Belzner, H. Ihmels, L. Pauletto, M. Noltemeyer, J. Org. Chem. 1996, 61, 3315-3319.
12. [1l] C. Käpplinger, R. Beckert, W. Günther, H. Görls, Liebigs Ann. Chem. 1997, 617-622.
13. [1m] K. Harada, M. Oda, A. Matsushita, M. Shirai, Synlett 1998, 431-433.
14. [1n] H. H. Karsch, P. A. Schlüter, F. Bienlein, M. Herker, E. Witt, A. Sladek, M. Heckel, Z. Anorg. Allg. Chem. 1998, 624, 295-309.
15. [2a] G. van Koten, K. Vrieze, Adv. Organomet. Chem. 1982, 21, 151-239.
16. [2b] K. Vrieze, J. Organomet. Chem. 1986, 300, 307-326.
17. [3a] L. K. Johnson, C. M. Killian, M. Brookhart, J. Am. Chem. Soc. 1995, 117, 6414-6415.
18. [3b] C. M. Killian, D. J. Tempel, L. K. Johnson, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 11664-11665.
19. [3c] L. K. Johnson, S. Mecking, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 267-268.
20. [3d] C. M. Killian, L. K. Johnson, M. Brookhart, Organometallics 1997, 16, 2005-2007.
21. [3e] A. S. Abu-Surrah, B. Rieger, Angew Chem. 1996, 108, 2627-2629; Angew. Chem. Int. Ed. Engl. 1996, 35, 2475-2477.
22. [3e] A. S. Abu-Surrah, B. Rieger, Angew Chem. 1996, 108, 2627-2629; Angew. Chem. Int. Ed. Engl. 1996, 35, 2475-2477.
23. [3f] W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1075-1095; Angew. Chem. Int. Ed. 1997, 36, 1047-1067.
24. [3f] W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1075-1095; Angew. Chem. Int. Ed. 1997, 36, 1047-1067.
25. [4a] R. van Asselt, C. J. Elsevier, Organometallics 1992, 11, 1999-2001.
26. [4b] R. van Asselt, E. E. C. G. Gielens, R. E. Rülke, K. Vrieze, C. J. Elsevier, J. Am. Chem. Soc. 1994, 116, 977-985.
27. [4c] R. van Asselt, C. J. Elsevier, Tetrahedron 1994, 50, 323-334.
28. [4d] A. LaPointe, M. Brookhart, Organometallics 1998, 17, 1530-1537.
29. [4e] R. van Beelzen, R. A. Klein, H. Kooijman, N. Veldman, A. L. Spek, C. J. Elsevier, Organometallics 1998, 17, 1812-1825.
30. R. Faust, C. Weber, submitted.
31. Mono alkynyl DADs in form of dinuclear μ-(pent-3-yne-1,2-diimine-1,5-diyl) transition metal complexes are known. See: [6a] K. Onitsuka, H. Ogawa, T. Joh, S. Takahashi, Y. Yamamoto, H. Yamazaki, J. Chem. Soc., Dalton Trans. 1991, 1531-1536.
32. [6b] K. Onitsuka, K. Yanai, F. Takei, T. Joh, S. Takahashi, Organometallics 1994, 13, 3862-3867.
33. The parent all-carbon π-system, namely 2,3-diethynyl-1,3-butadiene, has been described. See: H. Hopf, M. Theurig, P. G. Jonas, P. Bubenitschek, Liebigs Ann. 1996, 1301-1311.
34. W. Kaim, A. Klein, S. Hasenzahl, H. Stoll, S. Zális, J. Fiedler, Organometallics 1998, 17, 237-247.
35. [9a] B. J. Wakefield in Houben-Weyl: Methoden der Organischen Chemie (Ed.: E. Schaumann), Thieme. Stuttgart, 1993; Vol. E8a; p 61-67.
36. [9b] K. Kirschke in Houben-Weyl: Methoden der Organischen Chemie (Ed.: E. Schaumann), Thieme. Stuttgart, 1994; Vol. E8b; p 472-474.
37. K. Yang, R. J. Lachicotte, R. Eisenberg, Organometallics 1997, 16, 5234-5243.
38. R. Faust, B. Göbelt, Tetrahedron Lett. 1997, 38, 8017-8020.
39. R. Faust, B. Göbelt, C. Weber, Synlett 1998, 64-66.
40. R. Faust, C. Weber, V. Fiandanese, G. Marchese, A. Punzi, Tetrahedron 1997, 53, 14655-14670.
41. The beneficial steric properties of the triisopropylsilyl group have been reviewed. See: C. Rücker, Chem. Rev. 1995, 95, 1009-1064.
42. R. Faust, B. Göbelt, in preparation.
43. D. Lindauer, R. Beckert, M. Döring, P. Fehling, H. Görls, J. Prakt. Chem. 1995, 337, 143-152.
44. [17a] V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585-9595.
45. [17b] V. Farina in Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel; F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995; Vol. 12; p 200.
46. [17c] V. Farina, Pure Appl. Chem. 1996, 68, 73-78. - See also:
47. [17d] R. Faust, B. Göbelt, J. Prakt. Chem. 1998, 340, 90-93.
48. [18a] J. Scholz, B. Richter, R. Goddard, C. Krüger, Chem. Ber. 1993, 126, 57-61.
49. [18b] J. Wunderle, J. Scholz, R. Fröhlich, Z. Kristallogr. 1993, 205, 277-279.
50. S. Bachrach, M. Liu, J. Am. Chem. Soc. 1991, 113, 7929-7937.
51. J. J. Keijsper, H. van der Poel, L. H. H. Polm, G. van Koten, K. Vrieze, Polyhedron 1983, 2, 1111-1116.
52. C. J. M. Huige, A. L. Spek, J. L. de Boer, Acta Crystallogr. 1985, C41, 113-116.
53. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
54. [23a] R. Faust, E. D. Glendening, A. Streitwieser, K. P. C. Vollhardt, J. Am. Chem. Soc. 1992, 114, 8263-8268.
55. [23b] E. D. Glendening, R. Faust, A. Streitwieser, K. P. C. Vollhardt, F. Weinhold, J. Am. Chem. Soc. 1993, 115, 10952-10957.
56. 13C-NMR spectra of the compounds.
57. I. Hargittai, R. Seip, Acta Chem. Scand., Ser. A 1976, 30, 540-546.
58. O. Exner, J. M. Kliegman, J. Org. Chem. 1971, 36, 2014-2015.
59. H. torn Dieck, I. W. Renk, Chem. Ber. 1971, 104, 92-109.
60. O. Borgen, B. Mestvedt, I. Skanvik, Acta Chem. Scand., Ser. A 1976, 30, 43-46.
61. S. H. Lin, H.-Y. Sheng, Y. Z. Huang, Synthesis 1991, 235-236.
62. [30a] J. Simonet, H. Lund, Bull. Soc. Chem. Fr. 1975, 2547-2554.
63. [30b] K. Boujlel, J. Simonet, Tetrahedron Lett. 1985, 26, 3005-3006.
64. [30c] R. van Asselt, C. J. Elsevier, C. Amatore, A. Jutand, Organometallics 1997, 16, 317-328.
65. [30d] B. de Klerk-Engels, F. Hartl, K. Vrieze, Inorg. Chim. Acta 1997, 254, 239-250.
66. C. Boudon, J. P. Gisselbrecht, M. Gross, J. Anthony, A. M. Boldi, R. Faust, T. Lange, D. Philp, J.-D. Van Loon, F. Diederich, J. Electroanal. Chem. 1995, 394, 187-197.
67. C. Mansch, A. Leo, S. H. Unger, K. H. Kim, D. Nikaitani, E. J. Lien, J. Med. Chem. 1973, 16, 1207-1216.
68. A. Hilger, J.-P. Gisselbrecht, R. R. Tykwinski, C. Boudon, M. Schreiber, R. E. Martin, H. P. Lüthi, M. Gross, F. Diederich, J. Am Chem. Soc. 1997, 119, 2070-2078.
69. MacSpartan, V.1.1.7., Wavefunction Inc., Irvine CA 92612 (USA).
70. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, 3. Ed., Pergamon Press, Oxford, 1988.
71. U. T. Mueller-Westerhoff, M. Zhou, J. Org. Chem. 1994, 59, 4988-4992.
72. [37a] T. Ukai, H. Kawazura, Y. Ishii, J. Bonnett, J. A. Ibers, J. Organomet. Chem. 1974, 65, 253-266.
73. [37b] M. Rettig, P. M. Maitlis, Inorg. Synth. 1990, 28, 110.