Preparation of thiocyanates and isothiocyanates from alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/n-Bu4NSCN system

Tetrahedron

Volumn 62, Issue 23, 2006, Pages 5498-5501

  Iranpoor, Nasser ^a   Firouzabadi, Habib ^a   Nowrouzi, Najmeh ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Alcohol; DDQ; Isothiocyanation; Tetrahydropyranyl ether; Thiocyanation; Thiol; Trimethylsilyl ether; Triphenylphosphine

Indexed keywords

ALCOHOL DERIVATIVE; BENZOQUINONE DERIVATIVE; THIOCYANIC ACID DERIVATIVE; THIOL DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; MITSUNOBU REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STOICHIOMETRY; THIN LAYER CHROMATOGRAPHY;

EID: 33646200265     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.030     Document Type: Article

References (40)

1. Castro B.R. Org. React. 29 (1983) 1
2. Grundman C. Methoden der Organischen Chemie (Houben-Weyl), Band E5 (1985), Georg. Thieme, Stuttgart p 1474
3. Brett D., Downie I.M., and Lee J.B. J. Org. Chem. 32 (1967) 855
4. Castro B., and Selve C. Bull. Soc. Chim. Fr. (1971) 2296
5. Boigegrain R., Castro B., and Selve C. Tetrahedron Lett. 30 (1975) 2529
6. Davis R., and Untch K.G. J. Org. Chem. 46 (1981) 2985
7. Mitsunobu O. Synthesis (1981) 1
8. Hughes D.L. Org. React. 42 (1992) 335
9. Loibner H., and Zbiral E. Helv. Chim. Acta 59 (1976) 2100
10. Leblanc B.L., and Jursic B.C. Synth. Commun. 28 (1998) 3591
11. Newman A.A. Chemistry and Biochemistry of Thiocyanic Acid and its Derivatives. 1st ed. (1975), Academic, New York, NY
12. Iranpoor N., Firouzabadi H., Akhlaghinia B., and Azadi R. Synthesis (2004) 92
13. Tamura Y., Kawasaki T., Adachi M., Tanio M., and Kita Y. Tetrahedron Lett. (1977) 4417
14. Iranpoor N., Firouzabadi H., and Shaterian H.R. J. Chem. Res., Synop. (1999) 676
15. Iranpoor N., Firouzabadi H., and Shaterian H.R. Tetrahedron Lett. 43 (2002) 3439
16. Iranpoor N., Firouzabadi H., and Shaterian H.R. Synlett (2000) 65
17. Guram A.S. Synlett (1993) 259
18. Ando T., Clark J.H., Cork D.G., Fujita M., and Kimura T. J. Org. Chem. 52 (1987) 681
19. Reeves W.P., and McClusky J.V. Tetrahedron Lett. 24 (1983) 1585
20. Landini D., Maia A., Montanari F., and Rolla F. J. Org. Chem. 48 (1983) 3774
21. Lehmkuhl H., Rabet F., and Hauchild K. Synthesis (1977) 184
22. Kondo S., Takeda Y., and Tsuda K. Synthesis (1988) 403
23. Kondo S., Takeda Y., and Tsuda K. Synthesis (1989) 862
24. Iranpoor N., Firouzabadi H., Aghapour Gh., and Vaes zadeh A.R. Tetrahedron 58 (2002) 8689
25. Iranpoor N., Firouzabadi H., Akhlaghinia B., and Nowrouzi N. J. Org. Chem. 69 (2004) 2562
26. Iranpoor N., Firouzabadi H., Akhlaghinia B., and Nowrouzi N. Tetrahedron Lett. 45 (2004) 3291
27. Akhlaghinia B. Synthesis (2005) 1955
28. Kodomari M., Kuzuoka T., and Yoshitomi S. Synthesis (1983) 141
29. Guy R.G., and Pearson I. J. Chem. Soc., Perkin Trans. 2 (1973) 1359
30. Vass A., and Szalontai G. Synthesis (1986) 817
31. Lindhorst T.K., and Kieburg C. Synthesis (1995) 1228
32. Parks T.E., and Spurlock L.A. J. Org. Chem. 38 (1973) 3922
33. Woodgate P.D., Peter H.H., and Richard S.R. Synthesis (1977) 463
34. Toste F.D., Stefano V.D., and Still I.W.J. Synth. Commun. 25 (1995) 1277
35. Mandeelaire A., and Fort Y. Synth. Commun. 28 (1998) 583
36. Burski J., Kieszkowski J., Michaski J., Pakulski M., and Skowroska A. Tetrahedron 39 (1983) 4175
37. Burski J., Kieszkowski J., Michaski J., Pakulski M., and Skowroska A. J. Chem. Soc., Chem. Commun. (1973) 940
38. Greene T.W., and Wutz P.G.M. Protective Group in organic Synthesis. 2nd ed. (1991), Wiley, New York, NY
39. Lalonde M., and Chan T.H. Synthesis (1985) 817
40. Kocienski P.J. Protecting Group (1994), Thieme, New York, NY