Crystal structure of an imine–SnCl4 complex. The intermediate in catalytic aziridination reactions

(Note: The full text of this document is currently only available in the PDF Version )

Kaare G. Rasmussen, Rita G. Hazell and Karl Anker Jørgensen


Abstract

An imine–SnCl4 complex, which is an intermediate in Lewis acid catalysed aziridination reactions, is isolated and characterised by X-ray diffraction; the structure and catalytic properties of the complex are discussed.


References

  1. (a) K. B. Hansen, N. S. Finney and E. N. Jacobsen, Angew. Chem., Int. Ed. Engl., 1995, 34, 676 CrossRef CAS; (b) K. G. Rasmussen and K. A. Jørgensen, J. Chem. Soc., Chem. Commun., 1995, 1401 RSC; (c) M. Moran, G. Bernardinelli and P. Müller, Helv. Chem. Acta, 1996, 78, 2048 Search PubMed; (d) H.-J. Ha, K.-H. Kang, J.-M. Suh and Y.-G. Ahn, Tetrahedron Lett., 1996, 37, 7069 CrossRef CAS; (e) Z. Zhu and J. H. Esperson, J. Am. Chem. Soc., 1996, 118, 9901 CrossRef CAS; J. Org. Chem. 1995, 60, 7090 Search PubMed; (f) L. Casarrubios, J. A. Pérez, M. Brookhart and J. L. Tempelton, J. Org. Chem., 1996, 61, 8358 CrossRef CAS; (g) V. K. Aggerwal, A. Thompson, R. V. H. Jones and M. C. H. Standen, J. Org. Chem., 1996, 61, 8368 CrossRef CAS; (h) R. Bartnik and G. Mloston, Synthesis, 1983, 924 CrossRef CAS; (i) K. G. Rasmussen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 1, 1997, 1287 RSC.
  2. D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742 CrossRef CAS; J. Org. Chem., 1991, 56, 6744 Search PubMed; D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328 Search PubMed; D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726 CrossRef CAS; A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189 CrossRef CAS; Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326 CrossRef CAS; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889 CrossRef CAS; J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517 CrossRef CAS; K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001 RSC; K. Noda, N. Hosoya, R. Irie and T. Katsuki, Synlett, 1993, 469 CrossRef CAS; P. Müller, C. Baud and Y. Jacueier, Tetrahedron, 1996, 52, 1543 CrossRef CAS.
  3. Acid-catalysed isomerisation of imines has been observed before: D. Y. Curtin and J. W. Hausser, J. Am. Chem. Soc., 1961, 83, 3474 Search PubMed; G. A. Olah and D. J. Donovan, J. Org. Chem., 1978, 43, 860 CrossRef CAS.
  4. A search in the CCDA data file gave only one complex with SnCl4 coordinated to a nitrogen and an oxygen atom of an organic ligand(s): P. Domiano, A. Musatti, N. Nardelli, C. Pelizzi and G. Predieri, Inorg. Chem. Acta, 1980, 9, 38 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.