Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

S$_H$2 Reaction on Silicon-Carbon Bond in the Photoreactions of 2, 3-Benzo-1, 1-diphenyl(or dimethyl)-1-sila-2-cyclobutene with Carbonyl Compounds

  • Kang, Kyung-Tai (Department of Chemical Education, College of Education, Busan National University) ;
  • Okazaki, Renji (Department of Chemistry, Faculty of Science, The University of Tokyo) ;
  • Inamoto, Naoki (Department of Chemistry, Faculty of Science, The University of Tokyo)
  • Published : 1984.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

The photoreaction of 2, 3-benzo-1, 1-diphenyl (or dimethyl)-1-sila-2-cyclobutene (9 or 10) with an aldehyde or ketone results in 1:1 cycloadduct of [4 + 2] type. In the reactions of 2, 3-benzo-1, 1-dimethyl-1-sila-2-cyclobutene (10) with acetone and butanone, another 1:1 adducts (13) were also formed, respectively. The following facts indicate that the formation of adduct involves an attack of a triplet carbonyl compound on the silicon of the benzosilacyclobutene, an $S_H2$ process. (1) Even when the reaction of 9 with acetophenone was carried out under conditions such that more than 99% of incident light was absorbed only by acetophenone using the filter solution of aq. cupric sulfate, the same adduct was still formed. (2) When the reaction of 9 with acetone was carried out under oxygen atmosphere, only trace amount of adduct was formed.

Keywords

References

  1. Angew. Chem. Int. Ed. Engl. v.14 L. Jutzi
  2. Chem. Soc. Rev. v.9 R. L. Funk;K. P. C. Vollhardt
  3. Tetrahedron v.37 T. Kametani;H. Nemoto
  4. Tetrahedron Lett. P. B. Valkovich;W. P. Weber
  5. J. Organometal. Chem. v.219 D. Tzeng;R. H. Fong;H. S. D. Soysa;W. P. Weber
  6. Tetrahedron Lett. G. Bertrand;G. Manuel;P. Mazerolles
  7. Tetrahedron Lett. v.7 T. J. Barton;G. T. Burns;E. V. Arnold;J. Clardy
  8. J. Organometal. Chem. v.118 M. Ishikawa;T. Fuchikami;M. Kumada
  9. J. Organometal. Chem. v.149 M. Ishikawa;T. Fuchikami;M. Kumada
  10. J. Organometal. Chem. v.179 M. Ishikawa;H. Sugisawa;K. Yamamoto;M. Kumada
  11. Tetrahedron Lett. R. Okazaki;K. T. Kang;N. Inamoto
  12. Kagaku No Ryoiki v.29 H. Sakurai
  13. J. Organometal. Chem. v.9 C. Eaborn;D. R. M. Walton;M. Chan
  14. Tetrahedron Lett. H. Sakurai;A. Hosomi;M. Kumada
  15. J. Organometal. Chem. v.63 S. O. A. Rizvi;B. D. Gupta;W. Adcock;D. Doddnel;W. Kitching
  16. J. Chem. Soc. Dalton C. S. Chundy;M. F. Lapport;T. R. Spalding
  17. Tetrahedron Lett. A. Padwa
  18. J. Amer. Chem. Soc. v.87 S. G. Cohen;R. J. Baumgarten
  19. J. Amer. Chem. Soc. v.87 C. Walling;M. J. Gibian
  20. J. Chem. Soc. Perkin Trans. v.1 R. Okazaki;K. Tamura;Y. Hirabayashi;N. Inamoto
  21. Trans. Faraday Soc. v.66 S. H. Band;I. M. T. Davison
  22. J. Amer. Chem. Soc. v.94 A. Hosomi;H. Sakurai
  23. Acc. Chem. Res. v.8 L. E. Gusei'nikov;N. S. Nametkin;V. M. Vdokin
  24. Chem. Lett. A. Hosomi;H. Sakurai
  25. Free Radicals v.2 H. Sakurai;J. K. Kochi(Ed.)
  26. J. Amer. Chem. Soc. v.86 H. Gilman;W. H. Atwell
  27. Chem. Rev. v.79 L. E. Gusel'nikov;N. S. Nametkin
  28. Acc. Chem. Res. v.15 H. F. Schaefer III
  29. Bull. Chem. Soc. Jpn. v.52 R. Okazaki;K. Sunagawa;K.-T. Kang;N. Inamoto
  30. Bull. Chem. Soc. Jpn. v.52 K-T. Kang;R. Okazaki;N. Inamoto
  31. Yuki Gosei Kagaku Kyokai Shi v.34 R. Okazaki
  32. Synthesis W. Oppolzer