A new and convenient method of generating alkyl isocyanates from alcohols, thiols, and trimethylsilyl ethers using a 2,4,6-trichloro [1,3,5] triazine/n-$Bu_4NOCN$

A new and convenient method of generating alkyl isocyanates from alcohols, thiols, and trimethylsilyl ethers using a 2,4,6-trichloro [1,3,5] triazine/n-$Bu_4NOCN$

Alkyl isocyanates are prepared in good to excellent yields by treatment of alcohols, thiols, and trimethylsilyl ethers with 2,4,6-trichloro[l,3,5] triazine/n-Bu4NOCN in acetonitrile. This method is highly selective for conversion of 1° alcohols to alkyl isocyanates in the presence of 2° and 3° alcohols, thiols, and trimethylsilyl ethers.

___

  • 1. H. Ulrich, "Chemistry and Technology of Isocyanates", Wiley, New York (1996).
  • 2. S. Ozaki, Chem. Rev. 72, 457-69 (1977).
  • 3. B.A. Arbuzov and N.N. Zobova, Synthesis. 7, 433-50 (1982).
  • 4. W. Hentschel, Chem. Ber. 17, 1284 (1884).
  • 5. S. Werner, Annalen. 562, 75 -136 (1949).
  • 6. R.J. Slocombe, E.E. Hardy, J.H. Saunder and R.L. Jenkins, J. Am. Chem. Soc. 72, 1888-89 (1950).
  • 7. K. Kurita and Y. Iwakura, J. Org. Chem. 41, 2070-71 (1976).
  • 8. K. Kurita and Y. Iwakura, Org. Synth. Coll. 6, 715-19 (1988).
  • 9. H. Eckert and B. Forster, Angew. Chem., Int. Ed. Engl. 26, 894-95 (1987).
  • 10. L. Cotarca, P. Delogu, A. Nardelli and C.V. Sunji, Synthesis. 553-76 (1996).
  • 11. H.R. Kricheldorf, Synthesis. 649-50 (1970).
  • 12. H.R. Kricheldorf, Angew. Chem. 84, 107 (1972).
  • 13. M. Sakamoto, M. Mochizuki and M. Yoshioka, JP10072428 (1998).
  • 14. G. Greber and H.R. Kricheldorf, Angew. Chem. 80, 1028-29 (1968).
  • 15. H.A. Staab and W. Benz, Angew. Chem. 73, 66 (1961).
  • 16. R. Bonjouklian and R.A. Ruden, J. Org. Chem. 42, 4095-4103 (1977).
  • 17. C. Kaiser and J. Weinstock, Org. Synth. 51, 48 (1971).
  • 18. S. Heyden and G. Wilbert, Chem. Ind. 33, 1406 (1967).
  • 19. S. Bittner, S. Grinberg and I. Kartoon, Tetrahedron Lett. 15, 1965-68 (1974).
  • 20. F.A. Daniher, J. Org. Chem. 34, 2908-11 (1969).
  • 21. N. Iranpoor, H. Firouzabadi, Gh. Aghapour and A.R. Vaezzade, Tetrahedron. 58, 8689-93 (2002).
  • 22. N. Iranpoor, H. Firouzabadi, B. Akhlaghinia and N. Nowrouzi, J. Org. Chem. 69, 2562-64 (2004).
  • 23. N. Iranpoor, H. Firouzabadi, B. Akhlaghinia, and N. Nowrouzi, Tetrahedron Lett. 45, 3291-94 (2004).
  • 24. B. Akhlaghinia and A.R. Pourali, Synthesis. 1747-49 (2004).
  • 25. B. Akhlaghinia, Phosphorous, Sulfur Silicon Rel. 179, 1783-86 (2004).
  • 26. B. Akhlaghinia, Phosphorous, Sulfur Silicon Rel .180,1601-04 (2005).
  • 27. B. Akhlaghinia, Synthesis. 1955-58 (2005).
  • 28. B. Akhlaghinia and E. Roohi, Lett. Org. Chem. 2, 725-30 (2005).
  • 29. B. Akhlaghinia and E. Roohi, Lett. Org. Chem. 3, 220-24 (2006).
  • 30. K. Venkataraman and D.R. Wagle, Tetrahedron Lett. 20,3037-40 (1979).
  • 31. Z.J. Kaminski, P. Paneth and J. Rudzinski, J. Org. Chem. 63, 4248-55 (1998).
  • 32. J.E. Kaminska, Z.J. Kaminski and J. Gora, Synthesis. 593-96 (1999).
  • 33. S. Masala and M. Taddei, Org. Lett. 1355-57 (1999).
  • 34. L. De Luca, G. Giacomelli and M. Taddei, J. Org. Chem. 66, 2534-37 (2001).
  • 35. M. Falorni, A. Porcheddu and M. Tadei, Tetrahedron Lett. 40, 4395-96 (1999).
  • 36. M. Falorni, G. Giacomelli, A. Porcheddu and M. Taddei, J. Org. Chem. 64, 8962-64 (1999).
  • 37. L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett. 4, 553-55 (2002).
  • 38. B.P. Bandgar and S. Pandit, Tetrahedron Lett. 43, 3413-14 (2002).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

A Convenient Method for the Preparation of 2-Aminobenzophenone Derivatives under Ultrasonic Irradiation

Javad SAFAEI-GHOMI, Manouchehr FADAEIAN, Alireza HATAMI

Electron affinities, solvation energies and redox potentials of some chalcones: Substituents' effect and correlation with semi-empirical MO energies

Abdur RAHMAN, Rumana QRESHI, Mehvish KIRAN, Farzana Latif ANSARI

Plasma-Initiated Polymerization of (2-Methacryloyloxyethyl) Thrimethyl Ammonium Chloride

Yangang HE, Gang LI, Jing MIAO, Xueqing YU, Fang YANG

A New and Convenient Method of Generating Alkyl Isocyanates from Alcohols, Thiols, and Trimethylsilyl Ethers Using a 2,4,6-Trichloro[1,3,5] Triazine/n-Bu4NOCN

Batool AKHLAGHINIA, Sima SAMIEI

Electrochemical Characteristics of a 7-Ferrocenyl(carbonyloxy)-1- Heptanethiol-Modified Gold Electrode

Mohammed Muzibur RAHMAN, İl Cheol JEON

Preparation and Characterization of an Atenolol Selective Electrode Based on a PVC Matrix Membrane

Nabil S. NASSORY, Shahbaz A. Maki And Mutaz A. ALI, Mutaz A. ALI

Synthesis and Characterization of Oligo-2-[(2-hydroxymethylphenylimino) methyl] phenol and Oligo-2-[(2-hydroxymethylphenylimino) methyl]-5-bromo-phenol

İsmet KAYA, Ayşe Erçağ And Süleyman ÇULHAOĞLU

Gold(III) Complex of Caffeine: Synthesis, Isolation and Spectroscopic Characterization

Bojidarka IVANOVA

Studies on the preparation of $alpha,omega$-telechelic polmerys by the combination of reverse atom transfer radical polymerization and atom transfer radical coupling processes

Binnur AYDOĞAN, Yusuf YAĞCI

Synthesis and Spectral Characterisation of Chloro Organotin(IV) di[3(2`-hydroxyphenyl)-5-(4-substituted phenyl) Pyrazolinates]

Umesh Nath TRIPATHI, Mohammad Safi AHMAD, Goriparthi VENUBABU