Alkanes to nitriles and α-iminoesters. Polyoxotungstate photocatalytic radical chain initiation

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

Zhanmiao Zheng and Craig L. Hill


Abstract

Irradiation of W10O324– or PW12O403–, alkanes and methyl cyanoformate in CH3CN solution produces either the corresponding nitriles or α-iminoesters with high selectivity, depending on the temperature, via a mechanism involving two roles for the polyoxotungstate.


References

  1. B. A. Arndtsen, R. G. Bergman, T. A. Mobley and T. H. Peterson, Acc. Chem. Res., 1995, 28, 154 CrossRef.
  2. R. H. Crabtree, Chem. Alkanes Cycloalkanes, 1992, 653 Search PubMed.
  3. R. H. Crabtree, S. H. Brown, C. A. Muedas, C. Boojamra and R. R. Ferguson, Chemtech, 1991, 21, 634 CAS.
  4. Activation and Functionalization of Alkanes, ed. C. L. Hill, Wiley, New York, 1989, pp. 1–372 Search PubMed.
  5. Selective Hydrocarbon Activation: Principles and Progress, ed. J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, VCH, New York, 1990, pp. 1–568 Search PubMed.
  6. (a) R. F. Renneke and C. L. Hill, J. Am. Chem. Soc., 1988, 110, 5461 CrossRef CAS; (b) R. F. Renneke, M. Pasquali and C. L. Hill, J. Am. Chem. Soc., 1990, 112, 6585 CrossRef CAS; (c) R. F. Renneke, M. Kadkhodayan, M. Pasquali and C. L. Hill, J. Am. Chem. Soc., 1991, 113, 8357 CrossRef CAS; (d) B. S. Jaynes and C. L. Hill, J. Am. Chem. Soc., 1993, 115, 12212 CrossRef CAS; (e) C. L. Hill, Synlett, 1995, 127 CrossRef CAS.
  7. (a) T. Yamase and T. Usami, J. Chem. Soc., Dalton Trans., 1988, 183 RSC; (b) D. Attanasio and L. Suber, Inorg. Chem., 1989, 28, 3779 CrossRef CAS; (c) E. Papaconstantinou, Chem. Soc. Rev., 1989, 18, 1 RSC; (d) D. Attanasio, L. Suber and K. Thorslund, Inorg. Chem., 1991, 30, 590 CrossRef CAS; (e) C. Tanielian, Coord. Chem. Rev., in press Search PubMed.
  8. Supplement C2: The Chemistry of Triple-Bonded Functional Groups, ed. S. Patai, Wiley, New York, 1994, vol. 2, pp. 1–1349 Search PubMed.
  9. (a) R. G. Weiss, in CRC Handbook of Organic Photochemistry and Photobiology, ed. W. M. Horspool and P.-S. Song, CRC Press, Boca Raton, FL, 1995, ch. 39, pp. 471–483 Search PubMed; (b) J. Guillet, in Degradable Polymers, ed. G. Scott and D. Gilead, Chapman & Hall, London, 1995, ch. 12 Search PubMed.
  10. G. Stork and P. M. Sher, J. Am. Chem. Soc., 1983, 105, 6765 CrossRef CAS.
  11. D. H. R. Barton, J. C. Jaszberenyi and E. A. Theodorakis, Tetrahedron, 1992, 48, 2613 CrossRef CAS.
  12. D. D. Tanner and N. J. Bunce, J. Am. Chem. Soc., 1969, 91, 3028 CrossRef CAS.
  13. D. D. Tanner and P. M. Rahimi, J. Org. Chem., 1979, 44, 1674 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.