DOI QR코드

DOI QR Code

C-C Bond Cleavage of 8-Quinolinyl Alkyl Ketone by $\sigma,\eta^{3-}$-Allyl Rhodium(III) Complex

  • 발행 : 1997.08.20

초록

Bis(ethylene)rhodium(Ⅰ) chloride dimer reacted with vinylcyclopropane to give σ,η3-allylrhodium(Ⅲ) complex 3. Complex 3 underwent C-C bond cleavage of 8-quinolinyl ethyl ketone 11, to form η3-1,3-dimethylallylrhodium(Ⅲ) complex 8, which was reductively eliminated by trimethyl phosphite to give 8-quinolinyl-1-methylbut-2-enyl ketone (10). More sterically hindered 8-quinolinyl alkyl ketones were allowed to react with complex 3 to afford corresponding alkenes as well as a mixture of complex 8 and η3-1-ethylallyl rhodium(Ⅲ) complex 19, identified as 10 and 8-quinolinyl-pent-2-enyl ketone (20) after reductive elimination. 8-Quinolinyl alkyl ketone bearing a sterically hindered alkyl group showed less reactivity for C-C bond cleavage and higher 20/10 ratio compared with those having a less sterically hindered alkyl group, such as 8-quinolinyl ethyl ketone (11).

키워드

참고문헌

  1. Chem. Lett. v.927 Murakami, M.;Nishida, S.
  2. Tetrahedron Lett. v.23 Morizawa, Y.;Oshima, K.;Nozaki, H.
  3. J. Chem. Soc. Perkin Ⅱ v.962 Alcock, N. W.;Brown, J. M.;Connely, J. A.;Williamson, D. H.
  4. Synlett v.941 Ryu, I.;Ikura, K.;Tamura, Y.;Maenaka, J.;Ogawa, A.;Sonoda, N.
  5. Terahedron Lett. v.35 Hiroi, K.;Arinaga, Y.
  6. J. Am. Chem. Soc. v.87 Sarel, S.;Ben-Shoshan, R.;Kirson, B.
  7. Acc. Chem. Res. v.11 Sarel, S.
  8. Tetrahedron Lett. v.35 Hanzawa, Y.;Harada, S.;Nishio, R.;Taguchi, T.
  9. Tetrahedron Lett. v.37 Schulze, M. M.;Gokel, U.
  10. Syn. Comm. v.24 Gassman, P. G.;Lee, C.-J.
  11. J. Am. Chem. Soc. v.99 Salomon, R. G.;Salomon, M. F.;Kachinski, J. L. C.
  12. J. Am. Chem. Soc. v.96 Aumann, R.
  13. J. Am. Chem. Soc. v.112 Roell, B. C.;McDaniel, K. F.
  14. Organometallecs v.6 Bleeke, J. R.;Hays, M. K.
  15. J. Am. Chem. Soc. v.112 Bleeke, J. R.;Wittenbrink, R. J.;Clayton Jr. T. W.;Chang, M. Y.
  16. Tetrahedron Lett. v.36 Jun, C.-H.;Kang, J.-B.;Lim, Y.-G.
  17. Tetrahdron Lett. v.36 Jun, C.-H.;Lim, Y.-G.
  18. Tetrahedron Lett. v.30 Donaldson, W. A.;Ramaswamy, M.
  19. J. Am. Chem. Soc. v.106 Suggs, J. W.;Jun, C.-H.
  20. J. Am. Chem. Soc. v.108 Suggs, J. W.;Jun, C.-H.
  21. J. Chem. Soc. Chem. Comm. v.92 Suggs, J. W.;Jun, C.-H.
  22. Organometallics v.15 Jun, C.-H.
  23. Bull. Korean Chem. Soc. v.15 Jun, C.-H.;Koo, B.-T.;Kang, J.-B.;Kim, K.-J.
  24. Bull. Koeran Chem. Soc. v.12 Jun, C.-H.;Kang, J.-B.;Lim, Y.-G.
  25. Homogeneous Catalysis (2nd ed) Parshall, G. W.;Ittel, S. D.
  26. J.Organomet. Chem. v.390 Jun, C.-H.
  27. J. Chem. Soc. Chem. Comm. v.336 Porri, L.;Lionetti, G.;Allegra, A.;Immirzi, A.
  28. Can. J. Chem. v.45 Crawford, R. J.;Cameron, D. M.
  29. Inorg. Syn. v.14 van der Ent, A.;Onderdekinden, A. L.