Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Reactions of Triethylgermyldiphenylphosphine with Phenylisocyanate

Triethylgermyldiphenylphosphine과 Phenylisocyanate의 반응

  • Sung Woo Park (Chemistry Section, The National Institute of Scientific Investigation) ;
  • Il Kyu Lee (Department of Chemistry, Chung Ang University)
  • 박성우 (국립과학수사연구소 화학실) ;
  • 이일규 (중앙대학교 문리과대학 화학과)
  • Published : 1983.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Triethylgermyldiphenylphosphine was reacted with phenylisocyanate at various temperatures for three days in sealed ampoules. At $0^{\circ}C$, only N, N-diphenyluretidine-2,4-dione, a cyclic dimer of phenylisocyanate (35%), was formed. But at $20^{\circ}C$, phenylisocyanutrate, a cyclic trimer of phenylisocyanate (30%), was formed along with the dimer. At $50^{\circ}C$, diphenylcarbodiimide (55%) was given together with the compounds described above. At the higher reaction temperatures than $100^{\circ}C$, instead of the dimer and trimer of phenylisocyanate, 1,3,5-triphenyl-2,4,6-tris(phenylimino) hexahydro-1,3,5-triazine, a cyclic trimer of diphenylcarbodiimide (30%) and diphenylcarbodiimide (70%) were mainly produced. Triethylgermyldiphenylphosphine appears to act as a catalyst for the formation of the above cyclic compounds.

Triethylgermyldiphenylphosphine과 phenylisocyanate를 1:10 mole 비로 ampoule 속에서 혼합하여 여러 온도에서 반응시켰다. 그 결과 $0^{\circ}C$에서는 phenylisocyanate의 고리화 2합체인 N, N-diphenyluretidine-2,4-dione만이, $20^{\circ}C$에서는 phenylisocyanate의 고리화 3합체인 triphenylisocyanurate가 함께 생성되었으며, $50^{\circ}C$에서는 위의 생성물 이외에 diphenylcarbodiimide가 생성되었다. 또한 $100^{\circ}C$이상에서는 2합체는 생성되지 않고, diphenylcarbodiimide와 1,3,5-triphenyl-2,4,6-tris(phenylimino) hexahydro-1,3,5-triazine이 주로 생성되었다. 그리고 Triethylgermyldiphenylphosphine은 상기 고리 화합물들의 생성에 촉매로 작용하였다.

Keywords

References

  1. J. Korean Chem. Soc. v.15 S.Y. Han;I.K. Lee
  2. J. Dong-Guk Univ. v.14 I.K. Lee
  3. J. Chung-Ang Univ. v.22 I.K. Lee
  4. J. Korean Chem. Soc. v.23 B.S. Seo;I.K. Lee
  5. J. Korean Chem. Soc. v.24 B.S. Seo;K. J. Kim;I.K. Lee
  6. J. Korean Chem. Soc. v.25 G.J. Kim;I.K. Lee
  7. S.W. Park;I.K. Lee
  8. J. Chem. Soc. K. Itoh;I.K. Lee;Y. Ishii
  9. J. Chem. Soc. v.C K. Itoh;K. Matsuzaki;Y. Ishii
  10. J. Chem. Soc. v.A E.W. Abel;I.H. Sabnerwal
  11. J. Chem. Soc. A.J. Blocdworth;A.G. Davies
  12. J. Chem. Soc. T.A. George;K. Jones;M.F. Lappert
  13. Bull. Soc. Chem. France J.F. Labarre;J. Satge
  14. J. Chem. Soc. E.H. Brook;F. Glockling;K.A. Hooton
  15. J. Amer. Chem. Soc. v.88 R. E. Bukles;L.A. Mcgrew
  16. J. Org. Chem. D.F. Gavin;W.J. Schanbel;E. Kober;N.A. Robinson
  17. The Infrared Spectra of Complex Molecules L.J. Bellamy
  18. Inorg. Chem. v.4 R.E. Bukless;L.A. Allred
  19. Tran. Faraday. Soc. v.62 E.W. Abel;D.A. Armitage;D.B. Brady
  20. J. Org. Chem. v.30 R.T. Tsuzuki;Y. Iwakura
  21. Chem. Ber. v.97 J. Pump;E.G. Rochow