View PDF Version
 
DOI: 10.1039/A707559F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 2047-2054

The kinetics and mechanism of the phosphorus-catalysed dimerisation of acrylonitrile

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

C. Dennis Hall, Nicholas Lowther, Bruce R. Tweedy, Adam C. Hall and Gordon Shaw

Abstract

Isopropyl diarylphosphinites (Ar2POPri) catalyse the dimerisation of acrylonitrile (AN) to a mixture of cis- and trans-1,4-dicyanobut-1-ene (cis,trans-DCB-1), trans-1,4-dicyanobut-2-ene (DCB-2) and 2,4-dicyanobut-1-ene (MGN). The kinetics and mechanism of the reaction, which is a potential source of hexamethylenediamine, are reported in detail and the factors which govern rate and selectivity to DCB-1 and DCB-2 rather than MGN are elaborated.

References

  1. (a) J. D. McClure, J. Org. Chem., 1970, 35, 3045 CAS ; (b) R. Oda, T. Kawabata and S. Tanimoto, Tetrahedron Lett., 1964, 1653 CrossRef CAS ; (c) P. D. Beer, R. C. Edwards, C. D. Hall, J. R. Jennings and R. J. Cozens, Phosphorus Sulfur, 1983, 17, 283 Search PubMed ; (d) C. D. Hall, N. Lowther, B. R. Tweedy, R. Kayhanian, M. Piffl and G. Shaw, Phosphorus, Sulfur Silicon, 1996, 109–110, 521 CAS .
  2. J. R. Jennings and R. J. Cozens, Appl. Catalysis A, 1995, 124, 297 Search PubMed .
  3. J. R. Jennings, R. J. Cozens and K. Wade, Appl. Catalysis A, 1995, 130, 175 Search PubMed .
  4. J. R. Jennings and R. J. Cozens, Appl. Catalysis A, 1996, 135, 163 Search PubMed .
  5. A. I. Vogel, A Textbook of Practical Organic Chemistry, 1956, Longmans, London Search PubMed .
  6. C. D. Hall, B. R. Tweedy and N. Lowther, Phosphorus, Sulfur Silicon, 1997, 123, 341 CAS .
  7. J. R. Lloyd, N. Lowther and C. D. Hall, J. Chem. Soc., Perkin Trans. 2, 1985, 245 RSC .
  8. J. R. Lloyd, N. Lowther, G. Szabo and C. D. Hall, J. Chem. Soc., Perkin Trans. 2, 1985, 1813 RSC .
  9. C. D. Hall, P. D. Beer, R. L. Powell and M. P. Naan, Phosphorus, Sulfur Silicon, 1995, 105, 145 CAS .
  10. G. P. Schiemenz, Chem. Ber., 1966, 98, 514 .
  11. F. G. Mann and I. G. Millar, J. Chem. Soc., 1952, 4453 RSC .
  12. W. H. Dietsche, Tetrahedron Lett., 1966, 6347 CrossRef CAS .
  13. M. G. Futica and H. J. Harwood, J. Macromol. Sci., Chem., 1978, A12, 1099 Search PubMed .
Click here to see how this site uses Cookies. View our privacy policy here.