Domino reaction of lithiated allenes with nitriles

Chemical Communications

Volumn , Issue 18, 1998, Pages 1927-1928

  Langer, Peter ^a   Döring, Manfred ^b   Seyferth, Dietmar ^c  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002601305     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803040e     Document Type: Article

References (19)

1. For reviews on domino reactions, see: L. F. Tietze and U. Beifuss, Angew. Chem., 1993, 105, 137;
2. Angew. Chem., Int. Ed. Engl., 1993, 32, 131;
3. A. de Meijere and F. E. Meyer, Angew. Chem., 1994, 106, 2473;
4. Angew. Chem., Int. Ed. Engl., 1994, 33, 2379.
5. T. Tanase, T. Ohizumi, K. Kobayashi and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1992, 707.
6. (a) R. B. Bates, B. Gordon III, P. C. Keller and J. V. Rund, J. Org. Chem., 1980, 45, 168;
7. (b) G. Erker, M. Berlekamp, L. Lopez, M. Grehl, B. Schönecker and R. Krieg, Synthesis, 1994, 212;
8. M. Riedel and G. Erker, Synthesis, 1994, 1039;
9. G. Arrhenius, K. K. Baldridge, S. Richards-Gross and J. S. Siegel, J. Org. Chem., 1997, 62, 5522.
10. (a) S. Mathé and A. Rassat, Tetrahedron Lett., 1998, 39, 383;
11. (b) see also: L. N. Cherkasov and K. V. Balyan, Zh. Org. Khim., 1965, 1, 1811.
12. For domino reactions of dilithio compounds from our laboratory, see: (a) P. Langer, M. Döring, H. Görls and R. Beckert, Liebigs Ann./Receuil, 1997, 2553;
13. (b) P. Langer and M. Döring, Synlett, 1998, 396;
14. P. Langer and M. Döring, Synlett, 1998, 399;
15. P. Langer, J. Wuckelt, M. Döring and R. Beckert, Eur. J. Org. Chem., 1998, 1467.
16. D. Seyferth, P. Langer and M. Döring, Organometallics, 1995, 14, 4457.
17. M. S. Sigman and B. E. Eaton, Tetrahedron Lett., 1993, 34, 5367.
18. Triazines have been previously obtained by base induced cyclotrimerization of aryl nitrites: see C. Grundmann, in Methoden Org. Chem. (Houben-Weyl), 4th edn., Thieme, Stuttgart, New York, 1985, vol. E512, 1544.
19. For open-chained oligonitriles see M. Buhmann, M. H. Möller, U. Rodewald and E.-U. Würthwein, Chem. Ber., 1993, 126, 2467.