View PDF Version
 
DOI: 10.1039/A800781K (Paper) Reference Section for: Chem. Commun., 1998, 899-900

On the origin of 1,5-induction in tin(IV) halide-promoted reactions of 4-alkoxyalk-2-enylstannanes with aldehydes

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

Lindsay A. Hobson, Mark A. Vincent and Eric J. Thomas

Abstract

A combination of experiment and theory has identified both the allyltin trichlorides 3 (R2 = Bn, H) as key intermediates in tin(IV) chloride-promoted reactions of allylstannanes 1 (R2 = Bn, H) and the transition structures that are involved in their reactions with aldehydes.

References

  1. E. J. Thomas, Chem. Commun., 1997, 411 RSC.
  2. A. H. McNeill and E. J. Thomas, Synthesis, 1994, 322 CrossRef CAS.
  3. G. W. Bradley, D. J. Hallett and E. J. Thomas, Tetrahedron: Asymmetry, 1995, 6, 2579 CrossRef CAS.
  4. J. S. Carey and E. J. Thomas, Synlett, 1992, 585 CrossRef CAS.
  5. R. L. Beddoes, L. A. Hobson and E. J. Thomas, Chem. Commun., 1997, 1929 RSC.
  6. V. J. Jephcote and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1991, 429 RSC.
  7. A. T. Bottini, R. L. VanEtten and A. J. Davidson, J. Am. Chem. Soc., 1965, 87, 755 CrossRef CAS.
  8. L. D. Hall, P. R. Steiner and D. C. Miller, Can. J. Chem., 1979, 57, 38 CAS.
  9. W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257 CrossRef CAS; R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724 CrossRef CAS; M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163 CrossRef CAS; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213 CrossRef CAS; A. Stromberg, O. Gropen and U. Wahlgren, J. Comput. Chem., 1983, 4, 181 CrossRef an additional d-function with exponent 0.27 was used on tin.
  10. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. aghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, GAUSSIAN 94, Revision A.1, Gaussian, Inc., Pittsburgh, PA, 1995 Search PubMed.
  11. A. Bottoni, A. L. Costa, D. Di Tommaso, I. Rossi and E. Tagliavini, J. Am. Chem. Soc., 1997, 119, 121131 CrossRef CAS.
  12. K. Omoto, Y. Sawada and H. Fujimoto, J. Am. Chem. Soc., 1996, 118, 1750 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.