Domino reaction of lithiated allenes with nitriles†

Abstract

Addition of nitriles to dilithiated allenes results in a unique domino cyclization which involves the so far highest number of nitrile molecules added to an organolithium reagent to form unambiguously characterized oligomers.

References

1. For reviews on domino reactions, see: L. F. Tietze and U. Beifuss, Angew. Chem., 1993, 105, 137; Angew. Chem., Int. Ed. Engl., 1993, 32, 131; A. de Meijere and F. E. Meyer, Angew. Chem., 1994, 106, 2473; Angew. Chem., Int. Ed. Engl., 1994, 33, 2379.
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4. (a) S. Mathé and A. Rassat, Tetrahedron Lett., 1998, 39, 383; (b) see also: L. N. Cherkasov and K. V. Balyan, Zh. Org. Khim., 1965, 1, 1811.
5. 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; (b) P. Langer and M. Döring, Synlett, 1998, 396; (c) P. Langer and M. Döring, Synlett, 1998, 399; (d) P. Langer, J. Wuckelt, M. Döring and R. Beckert, Eur. J. Org. Chem., 1998, 1467.
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7. M. S. Sigman and B. E. Eaton, Tetrahedron Lett., 1993, 34, 5367.
8. Triazines have been previously obtained by base induced cyclotrimerization of aryl nitriles: see C. Grundmann, in Methoden Org. Chem.(Houben-Weyl), 4th edn., Thieme, Stuttgart, New York, 1985, vol. E512, 1544.
9. For open-chained oligonitriles see M. Buhmann, M. H. Möller, U. Rodewald and E.-U. Würthwein, Chem. Ber., 1993, 126, 2467.