On the reaction of acyl chlorides and carboxylic anhydrides with phosphazenes

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5638-5643

  Bosch, Imma ^a   González, Angel ^a   Urpí, Fèlix ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001536803     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951951b     Document Type: Article

References (39)

1. Molina, P.; Alajarín, M.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1993, 49, 5153. Molina, P.; Alajarín, M.; López-Leonardo, C. Tetrahedron Lett. 1991, 32, 4041.
2. Molina, P.; Alajarín, M.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1993, 49, 5153. Molina, P.; Alajarín, M.; López-Leonardo, C. Tetrahedron Lett. 1991, 32, 4041.
3. 5-azenes; phosphazenes are also called iminophosphoranes and phosphimines.
4. For example, see: Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 29. Bachi, M. D.; Vaya, J. J. Org. Chem. 1979, 44, 4393. Bachi, M. D.; Klein, J. J. Chem. Soc., Perkin Trans. 1 1983, 1925. Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc., Perkin Trans. 1 1990, 2193. Katritzky, A. R.; Zhang, G.; Jiang, J. J. Org. Chem. 1994, 59, 4556.
5. For example, see: Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 29. Bachi, M. D.; Vaya, J. J. Org. Chem. 1979, 44, 4393. Bachi, M. D.; Klein, J. J. Chem. Soc., Perkin Trans. 1 1983, 1925. Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc., Perkin Trans. 1 1990, 2193. Katritzky, A. R.; Zhang, G.; Jiang, J. J. Org. Chem. 1994, 59, 4556.
6. For example, see: Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 29. Bachi, M. D.; Vaya, J. J. Org. Chem. 1979, 44, 4393. Bachi, M. D.; Klein, J. J. Chem. Soc., Perkin Trans. 1 1983, 1925. Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc., Perkin Trans. 1 1990, 2193. Katritzky, A. R.; Zhang, G.; Jiang, J. J. Org. Chem. 1994, 59, 4556.
7. For example, see: Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 29. Bachi, M. D.; Vaya, J. J. Org. Chem. 1979, 44, 4393. Bachi, M. D.; Klein, J. J. Chem. Soc., Perkin Trans. 1 1983, 1925. Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc., Perkin Trans. 1 1990, 2193. Katritzky, A. R.; Zhang, G.; Jiang, J. J. Org. Chem. 1994, 59, 4556.
8. For example, see: Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 29. Bachi, M. D.; Vaya, J. J. Org. Chem. 1979, 44, 4393. Bachi, M. D.; Klein, J. J. Chem. Soc., Perkin Trans. 1 1983, 1925. Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc., Perkin Trans. 1 1990, 2193. Katritzky, A. R.; Zhang, G.; Jiang, J. J. Org. Chem. 1994, 59, 4556.
9. For reviews on phosphazene chemistry, see: Barluenga, J.; Palacios, F. Org. Prep. Proced. Int. 1991, 23, 1. Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353. Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993.
10. For reviews on phosphazene chemistry, see: Barluenga, J.; Palacios, F. Org. Prep. Proced. Int. 1991, 23, 1. Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353. Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993.
11. For reviews on phosphazene chemistry, see: Barluenga, J.; Palacios, F. Org. Prep. Proced. Int. 1991, 23, 1. Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353. Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993.
12. For reviews on phosphazene chemistry, see: Barluenga, J.; Palacios, F. Org. Prep. Proced. Int. 1991, 23, 1. Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353. Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993.
13. Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671. For a related paper, see: Bosch, I.; Urpí, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commum. 1995, 91.
14. Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671. For a related paper, see: Bosch, I.; Urpí, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commum. 1995, 91.
15. Although not indicated in Table 1, the reactions of entries 1 and 5 were repeated at 60°C, with phosphazene excess, but C-phosphonium salts were not detected either, while the normal carboxamides were isolated in 90-92% yields.
16. For a review, see: Hudson, H. R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: New York, 1990; Vol. 1, pp 385 and 473. For early studies: Henderson, W. A.; Streuli, C. A. J. Am. Chem. Soc. 1960, 20, 5791. Henderson, W. A.; Buckler, S. A. J. Am. Chem. Soc. 1960, 20, 5794. For illustrative examples, from ourselves: Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623. Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1990, 31, 7497.
17. For a review, see: Hudson, H. R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: New York, 1990; Vol. 1, pp 385 and 473. For early studies: Henderson, W. A.; Streuli, C. A. J. Am. Chem. Soc. 1960, 20, 5791. Henderson, W. A.; Buckler, S. A. J. Am. Chem. Soc. 1960, 20, 5794. For illustrative examples, from ourselves: Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623. Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1990, 31, 7497.
18. For a review, see: Hudson, H. R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: New York, 1990; Vol. 1, pp 385 and 473. For early studies: Henderson, W. A.; Streuli, C. A. J. Am. Chem. Soc. 1960, 20, 5791. Henderson, W. A.; Buckler, S. A. J. Am. Chem. Soc. 1960, 20, 5794. For illustrative examples, from ourselves: Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623. Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1990, 31, 7497.
19. For a review, see: Hudson, H. R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: New York, 1990; Vol. 1, pp 385 and 473. For early studies: Henderson, W. A.; Streuli, C. A. J. Am. Chem. Soc. 1960, 20, 5791. Henderson, W. A.; Buckler, S. A. J. Am. Chem. Soc. 1960, 20, 5794. For illustrative examples, from ourselves: Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623. Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1990, 31, 7497.
20. For a review, see: Hudson, H. R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: New York, 1990; Vol. 1, pp 385 and 473. For early studies: Henderson, W. A.; Streuli, C. A. J. Am. Chem. Soc. 1960, 20, 5791. Henderson, W. A.; Buckler, S. A. J. Am. Chem. Soc. 1960, 20, 5794. For illustrative examples, from ourselves: Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623. Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1990, 31, 7497.
21. Genkina, G. K.; Korolev, B. A.; Gilyanov, V. A.; Kabachnik, M. I. Zh. Obshch. Khim. 1971, 41, 80; Chem. Abstr. 1971, 75, 129120w.
22. Genkina, G. K.; Korolev, B. A.; Gilyanov, V. A.; Kabachnik, M. I. Zh. Obshch. Khim. 1971, 41, 80; Chem. Abstr. 1971, 75, 129120w.
23. 3PO, ca. 40% of 4, small amounts of phosphazenium salt, and no polar products at all.
24. The ratio between these two peaks depended on propanoyl chloride purity (whether freshly distilled or not), on the time elapsed before registering the first spectrum, and on the addition order of the reagents and their relative excess.
25. 1H NMR).
26. HP = 12.6 Hz).
27. 2COX are quenched with water at much shorter reaction times, when intermediates of type 5 may predominate, the amide yields are much lower (more polar products were mainly obtained).
28. - was isolated in 12% yield by column chromatography. We believe that part of the phosphazenium salt arises from the presence of acid impurities in the (water-sensitive) acid chloride.
29. 2Ph, instead of the tributylphosphazene, the spectra were analogous although the O-phosphonium species (that related with 9a) was much less abundant.
30. For reviews, see: Schaumann, E.; Scheiblich, S. In Houben-Weyl Methoden der organischen Chemie; G. Thieme-Verlag: Stuttgart, 1993; E 15/Teil 2. The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley: New York, 1980.
31. For reviews, see: Schaumann, E.; Scheiblich, S. In Houben-Weyl Methoden der organischen Chemie; G. Thieme-Verlag: Stuttgart, 1993; E 15/Teil 2. The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley: New York, 1980.
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37. Dermer, O. C.; King, J. J. Org. Chem. 1943, 8, 168. Also see: Maran, F.; Vianello, E.; D'Angeli, F.; Cavicchioni, G.; Vecchiati, G. J. Chem. Soc., Perkin Trans. 2 1987, 33. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375.
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