Dialkoxyphosphinyl-substituted enols of carboxamides

Journal of Organic Chemistry

Volumn 72, Issue 20, 2007, Pages 7605-7624

  Song, Jinhua ^a   Yamataka, Hiroshi ^b   Rappoport, Zvi ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SUBSTITUTION REACTIONS;

E-ISOMERS; LINEAR CORRELATION; SOLID PHOSPHONATES;

AMIDES;

ALKYL GROUP; AMIDE; ESTER DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SOLVENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; ISOMER; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 34848917529     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0710679     Document Type: Article

References (50)

1. Sklenak, S.; Apeloig, Y.; Rappoport, Z. J. Am. Chem. Soc. 1998, 120, 10359.
2. Frey, J.; Rappoport, Z. J. Am. Chem. Soc. 1996, 118, 3994.
3. Rappoport, Z.; Frey, J.; Sigalov, M.; Rochlin, E. Pure Appl. Chem. 1997, 69, 1933.
4. Mukhopadhyaya, J. K.; Sklenak, S.; Rappoport, Z. J. Am. Chem. Soc. 2000, 122, 1325.
5. Lei, Y. X.; Cerioni, G.; Rappoport, Z. J. Org. Chem. 2001, 66, 8379.
6. Song, J.; Rappoport, Z. The 10th European Symposium on Organic Reactivity (ESOR 10), Rome, Italy, July 25-30, 2005, Abstract book, p 46.
7. (a) Lei, Y. X.; Casarini, D.; Cerioni, G.; Rappoport, Z. J. Org. Chem. 2003, 68, 947.
8. (b) Lei, Y. X.; Casarini, D.; Cerioni, G.; Rappoport, Z. J. Phys. Org. Chem. 2003, 16, 525.
9. (c) Basheer, A.; Rappoport, Z. J. Org. Chem. 2004, 69, 1151.
10. Mukhopadhyaya, J. K.; Sklenak, S.; Rappoport, Z. J. Org. Chem. 2000, 65, 6856.
11. Basheer, A.; Yamataka, H.; Ammal, S. C.; Rappoport, Z. J. Org. Chem. 2007, 72, 5297.
12. Basheer, A.; Rappoport, Z. Submitted for publication.
13. (a) Simonsen, O.; Thorup, N. Acta Crystallogr. Sect. B 1979, 57, 1177.
14. (b) Basheer, A.; Rappoport, Z. Unpublished results.
15. Basheer, A.; Rappoport, Z. The 17th IUPAC Conference on Physical Organic Chemistry, Shanghai, China, August 15-20, 2004, Abstract IL-10, p 84.
16. (a) Breuer, E. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester, 1996; Vol. 4, Chapter 7, pp 694-698.
17. (b) Afarinkia, K.; Echenique, J.; Nyburg, S. C. Tetrahedron Lett. 1997, 38, 1663.
18. There are slightly related phosphato-substituted enols in biological systems such as phosphoenol pyruvate (Richard, J. P. In The Chemistry of Enols; Rappoport, Z., Ed.; Wiley: Chichester, 1990; Chapter 11).
19. We use the term "formal" since in solution the compounds exist an amide/enols (E and Z) mixtures and in the solid state they may have an amide or an enol structure.
20. Hamlet, Z.; Mychajlowskij, W. Chem. Ind. (London, UK) 1974, (20), 829.
21. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
22. Modro, A. M.; Modro, T. Can. J. Chem. 1999, 77, 890.
23. (a) Charton, M. In The Chemistry of Cyclobutanes; Rappoport, Z., Liebman, J. F., Eds.; Wiley: New York, 2005; Chapter 10, p 441.
24. (b) Katzhendler, J.; Ringel, I.; Karaman, R.; Zaher, H.; Breuer, E. J. Chem. Soc., Perkin Trans. 2 1997, 341.
25. (c) Taft, R. W., Jr. In Steric Effects in Organic Chemistry; Newman, M. S., Ed.; Wiley: New York, 1956; Chapter 13, p 619.
26. (a) Corbridge, D. C. E. Phosphorus. An Outline of its Chemistry, Biochemistry and Technology, 4th ed.; Elsevier: Amsterdam, 1990; Chapter 14.1.
27. (b) Gramstad, T. Spectrochim. Acta 1963, 19, 1363.
28. (c) Asknes, G.; Albriktsen, P. Acta Chem. Scand. 1966, 22, 1866.
29. (d) Gramstad, T.; Storesund, H. J. Spectrochim. Acta Part A 1970, 26A, 426.
30. (e) Bel'skii, V. E.; Bakeeva, R. F.; Kudryavtseva, L. A.; Kurguzova, M. A.; Ivanov, B. E. Zh. Obshch. Khim. (Eng. Transl.) 1975, 43, 2568.
31. (f) Raevskii, O. A.; Gilyazov, M. M.; Levin, Y. A., Zh. Obshch. Khim. 1978, 48, 1053.
32. (g) Bel'skii, V. E.; Ashrafullina, L. Kh. Zh. Obshch. Khim. (Engl. Transl.) 1979, 49, 1968.
33. (a) Genov, D. G.; Tebby, J. C. J. Org. Chem. 1996, 61, 2454.
34. (b) Alexandratos, M.; Zhu, X. Macromolecules 2005, 38, 5981.
35. (a) Belciug, M. P.; Modro, A. M.; Modro, T. A. J. Phys. Org. Chem. 1992, 5, 787.
36. (b) Belciug, M. P.; Modro, P. A.; Wessels, P. J. J. Phys. Org. Chem. 1993, 6, 523.
37. (c) Bourne, S.; Modro, A. M.; Modro, T. A. Phosphorus, Sulfur Silicon 1995, 102, 83.
38. Ta-Shma, R.; Schneider, H.; Mahajana, M.; Katzhendler, J.; Breuer, E. J. Chem. Soc., Perkin Trans. 2 2001, 1404.
39. (a) Abraham , M. H.; Duce, P. P.; Pirov, D. V.; Barratt, D. G.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 1355.
40. (b) Hickey, J. P.; Passino-Reader, D. R. Environ. Sci. Technol. 1991, 25, 1753.
41. (c) Raevsky, O. A.; Grigor'ev, V. Y.; Kireev, D. B.; Zefirov, N. S. Quant. Struct. Act. Relat. 1992, 11, 49.
42. Mishima, M.; Matsuoka, M.; Lei, Y. X.; Rappoport, Z. J. Org. Chem. 2004, 69, 5947.
43. Frey, J.; Rappoport, Z. Z. J. Org. Chem. 1997, 62, 8327.
44. Gaussian 98, Revision A.6: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.
45. (a) Becke, A. D. Phys. Rev. 1988, A38, 3098.
46. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
47. Apeloig, Y.; Arad, D.; Rappoport, Z. J. Am. Chem. Soc. 1990, 112, 9131.
48. Sklenak, S.; Apeloig, Y.; Rappoport, Z. J. Chem. Soc., Perkin Trans. 2 2000, 2269.
49. Yamataka, H.; Rappoport, Z. J. Am. Chem. Soc. 2000, 122, 9818.
50. Rappoport, Z.; Lei, Y. X.; Yamataka, H. Helv. Chem. Acta 2001, 84, 1401.