1,2,5,6-Tetrazocines from Nitrile Imines and tert-Butyl Isocyanide

Advanced Synthesis and Catalysis

Volumn 342, Issue 7, 2000, Pages 707-710

  Moderhack, Dietrich ^a   Daoud, Ali ^a   Ernst, Ludger ^b   Jones, Peter G ^b  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b Technischen Universitat   (Germany)

Author keywords

1,2,5,6 Tetrazocines; Heterocycles; Isocyanides; Nitrile imines; X Ray absorption spectroscopy

Indexed keywords

EID: 0347304578     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3897(200009)342:7<707::aid-prac707>3.3.co;2-u     Document Type: Article

References (26)

1. Review: D. Moderhack, Synthesis 1985, 1083
2. a) D. Moderhack, M. Lorke, Heterocycles 1987, 26, 1751;
3. b) D. Moderhack, M. Lorke, L. Ernst, D. Schomburg, Chem. Ber. 1994, 127, 1633
4. This pertains to the products that are formed by self-condensation of benzil monohydrazones and other α-oxo hydrazones; early examples for the erroneous 1,2,5,6-tetrazocine structure are collected in ref. [4a], more recent cases can be located in: a) A. Aydin, H. Feuer, Chim. Acta Turc. 1979, 7, 121; Chem. Abstr. 1980, 93, 220680g; b) C. Glidewell, D. Lloyd, K. W. Lumbard, J. Chem. Soc., Dalton Trans. 1987, 501
5. This pertains to the products that are formed by self-condensation of benzil monohydrazones and other α-oxo hydrazones; early examples for the erroneous 1,2,5,6-tetrazocine structure are collected in ref. [4a], more recent cases can be located in: a) A. Aydin, H. Feuer, Chim. Acta Turc. 1979, 7, 121; Chem. Abstr. 1980, 93, 220680g; b) C. Glidewell, D. Lloyd, K. W. Lumbard, J. Chem. Soc., Dalton Trans. 1987, 501
6. This pertains to the products that are formed by self-condensation of benzil monohydrazones and other α-oxo hydrazones; early examples for the erroneous 1,2,5,6-tetrazocine structure are collected in ref. [4a], more recent cases can be located in: a) A. Aydin, H. Feuer, Chim. Acta Turc. 1979, 7, 121; Chem. Abstr. 1980, 93, 220680g; b) C. Glidewell, D. Lloyd, K. W. Lumbard, J. Chem. Soc., Dalton Trans. 1987, 501
7. a) R. Pfleger, E. Garthe, K. Rauer, Chem. Ber. 1963, 96, 1827;
8. b) M. Brufani, W. Fedeli, G. Giacomello, A. Vaciago, Chem. Ber. 1963, 96, 1840;
9. c) R. A. Carboni, J. C. Kauer, J. E. Castle, H. E. Simmons, J. Am. Chem. Soc. 1967, 89, 2618;
10. d) R. N. Butler, D. M. Colleran, D. F. O'Shea, D. Cunningham, P. McArdle, A. M. Gillan, J. Chem. Soc., Perkin Trans. 1 1993, 2757
11. The material proved resistent not only to 6N-14N NaOH but also to oxidants such as potassium permanganate.
12. 3O 201.0902); 4-acetyl1-(p-tolyl)-1H-1,2,3-triazole has the same composition, but this species can be ruled out because of absence of m/z = 173 (loss of molecular nitrogen).
13. a) D. Moderhack, Liebigs Ann. 1996, 777;
14. b) Analogous amides have been obtained previously by ring cleavage of 1,2,3-triazolium ions: D. Moderhack, Liebigs Ann. Chem. 1989, 1271
15. Tetrazocines were absent, except for trace amounts observed in part when using cyclohexyl isocyanide (see Experimental).
16. D. Moderhack, A. Daoud, unpublished results.
17. Perhydro derivatives (1,2,5,6-tetrazocanes) are known, albeit in low number; for a monocyclic example, see: E. C. Taylor, H. M. L. Davies, J. Org. Chem. 1984, 49, 4415; for a tetrazocane unit fused to the N-N bond of pyrazole rings, see: P. Cabildo, R. M. Claramunt, P. Cornago, J. L. Lavandera, D. Sanz, N. Jagerovic, M. L. Jimeno, J. Elguero, I. Gilles, J.-L. Aubagnac, J. Chem. Soc., Perkin Trans. 2 1996, 701, and references cited therein
18. Perhydro derivatives (1,2,5,6-tetrazocanes) are known, albeit in low number; for a monocyclic example, see: E. C. Taylor, H. M. L. Davies, J. Org. Chem. 1984, 49, 4415; for a tetrazocane unit fused to the N-N bond of pyrazole rings, see: P. Cabildo, R. M. Claramunt, P. Cornago, J. L. Lavandera, D. Sanz, N. Jagerovic, M. L. Jimeno, J. Elguero, I. Gilles, J.-L. Aubagnac, J. Chem. Soc., Perkin Trans. 2 1996, 701, and references cited therein
19. This is to be understood as incorporation of the isocyanide carbon atom into the eight-membered ring; hence, the reaction reported by B. M. Ebert, I. K. Ugi, M. Grosche, E. Herdtweck, W. A. Herrmann, Tetrahedron 1998, 54, 11887, is not directly relevant.
20. W. Dieckmann, L. Platz, Ber. Dtsch. Chem. Ges. 1905, 38, 2986
21. D. Anderson Bowack, A. Lapworth, J. Chem. Soc. 1905, 87, 1854
22. G. W. Gokel, R. P. Widera, W. Weber, Org. Synth. 1976, 55, 96
23. R. Obrecht, R. Herrmann, I. Ugi, Synthesis 1985, 400
24. I. Ugi, R. Meyr, Chem. Ber. 1960, 93, 239
25. J. V. Jollimore, M. Vacheresse, K. Vaugham, D. L. Hooper, Can. J. Chem. 1996, 74, 254
26. G.M. Sheldrick, "SHELXL-97, A Program for Refining Crystal Structures", University of Göttingen, Germany, 1997