Synthesis of acyl azides using the Vilsmeier complex

Synthetic Communications

Volumn 33, Issue 4, 2003, Pages 607-611

  Sridhar, Radhakrishnan ^a   Perumal, Paramasivan T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

Acyl azide; Chloromethyleniminium ion; Nitrene; Nitrogen heterocycle

Indexed keywords

AZIDE; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; FOURIER ANALYSIS; INFRARED SPECTROSCOPY; MELTING POINT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0037232063     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120015815     Document Type: Article

References (25)

1. (a) Jones, G.; Stanforth, S.P. Org. React. 1997, 49, 1;
2. (b) Jutz, C. Advances in Organic Chemistry; Taylor, E.C., Ed.; John Wiley & Sons: New York, 1976; Vol. 9, p. 225;
3. (c) Marson, C.M. Tetrahedron 1992, 48, 3659.
4. (a) Majo, V.J.; Perumal, P.T. J. Org. Chem. 1998, 63, 7136;
5. (b) Selvi, S.; Perumal, P.T. Indian. J. Chem. Sec. B 2000, 39B, 163;
6. (c) Majo, V.J.; Perumal, P.T. J. Org. Chem. 1996, 61, 6523;
7. (d) Majo, V.J.; Perumal, P.T. Tetrahedron Lett. 1997, 38, 6889.
8. Lwowski, W. Chemistry of the Azido Group; Patai, S., Ed.; Interscience Publisher, John Wiley: New York, 1969; 503.
9. Guichard, G.; Semetey, V.; Didierjean, C.; Aubry, A.; Briand, J.P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702.
10. Chiyoda, T.; Iida, K.; Takatori, K.; Kaliwara, M. Synlett 2000, 10, 1427.
11. Horning, D.E.; Muchowski, J.M. Can. J. Chem. 1967, 45, 1247.
12. (a) Lee, J.G.; Kwak, K.H. Tetrahedron Lett. 1992, 33, 3165;
13. (b) Elmorsy, S.S. Tetrahedron Lett. 1995, 36, 1341.
14. (a) Rawal, V.H.; Zhong, H.M. Tetrahedron Lett. 1994, 35, 4947;
15. (b) Zhong, H.M. Diss. Abstr. Int. 1995, 56, 4895.
16. Wagner, R.B.; Zook, H.D. Synthetic Organic Chemistry; John Wiley: New York, 1953; 575.
17. a. Starks, C.M.; Liotta, C. Phase Transfer Catalysis; Academic Press: New York, 1978; 156.
18. b. Sakai, K.; Anselme, J. P. J. Org. Chem. 1971, 36, 2387.
19. Kricheldorf, H.R.; Leppert, E. Synthesis 1976, 329.
20. Macmillan, J.H.; Washburne, S.S. J. Org. Chem. 1973, 38, 2982.
21. Kaiser, C.; Weinstock, J. Org. Synth. 1971, 51, 48.
22. Van Reijendam, J.W.; Baardmann, F. Synthesis 1973, 413.
23. Thraot, M.T.; Mane, R.B.; Deshmukh, J.G.; Salunkhe, M.M.; Wadgaonkar, P.P. Indian J. Chem. Sec. B 1989, 28B, 186.
24. Jones, L.W.; Mason, J.P. J. Am. Chem. Soc. 1927, 49, 2528.
25. Weber, G.; Hauptmann, S.; Wilde, H.; Mann, G. Synthesis 1983, 191.