Kinetics and Mechanism of the Alkaline Hydrolysis of 2,4-Dinitrophenyl 4′-Hydroxyphenylpropiolate

European Journal of Organic Chemistry

Volumn , Issue 4, 1998, Pages 665-669

  Cevasco, Giorgio ^a   Pardini, Roberto ^a   Thea, Sergio ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

Acyl transfer reactions; Elimination addition mechanism; Ester hydrolysis

Indexed keywords

EID: 2742553388     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199804)1998:4<665::aid-ejoc665>3.0.co;2-f     Document Type: Article

References (21)

1. G. Cevasco, G. Guanti, A.R. Hopkins, S. Thea, A. Williams, J. Org Chem. 1985, 50, 479-484; S. Thea, G. Cevasco, G. Guanti, N. Kashefi-Naini, A. Williams. J. Org. Chem. 1985, 50, 1867-1872.
2. G. Cevasco, G. Guanti, A.R. Hopkins, S. Thea, A. Williams, J. Org Chem. 1985, 50, 479-484; S. Thea, G. Cevasco, G. Guanti, N. Kashefi-Naini, A. Williams. J. Org. Chem. 1985, 50, 1867-1872.
3. G. Cevasco, S. Thea, J. Org. Chem. 1994, 59, 6274-6278.
4. G. Cevasco, S. Thea, J. Org. Chem. 1995, 60, 70-73.
5. A. Williams, K.T. Douglas, Chem. Rev. 1975, 75, 627-649.
6. G. Cevasco, S. Thea, submitted for publication.
7. FigP, Biosoft, Cambridge, UK, 1991.
8. H. S. Arned, L. Fallon, J. Am. Chem. Soc. 1931, 61, 2374-2378.
9. P. Vlasak, J. Mindl, J. Chem Soc., Perkin Trans 2 1997, 1401-1403; A. Safraoui, M. Calmon, J.-P. Calmon, J. Chem. Soc., Perkin Trans. 2 1991, 1349-1352; T. J. Broxton, Aust J. Chem. 1985, 38, 77-83.
10. P. Vlasak, J. Mindl, J. Chem Soc., Perkin Trans 2 1997, 1401-1403; A. Safraoui, M. Calmon, J.-P. Calmon, J. Chem. Soc., Perkin Trans. 2 1991, 1349-1352; T. J. Broxton, Aust J. Chem. 1985, 38, 77-83.
11. P. Vlasak, J. Mindl, J. Chem Soc., Perkin Trans 2 1997, 1401-1403; A. Safraoui, M. Calmon, J.-P. Calmon, J. Chem. Soc., Perkin Trans. 2 1991, 1349-1352; T. J. Broxton, Aust J. Chem. 1985, 38, 77-83.
12. N. S. Isaacs, Physical Organic Chemistry, Longman S and T, Harlow, 1987, chapter 10.6.
13. D. H. Wadsworth, S. M. Geer, M. R. Detty, J. Org. Chem. 1987, 52, 3662-3668.
14. M. S. Newman, S. H. Merrill, J Am Chem. Soc. 1955, 77, 5549-5551.
15. J. Chenault, J. F. Dupin, Synthesis 1987, 498-499.
16. S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627-630.
17. L. Brandsma, Preparative Acetylenic Chemistry, Elsevier, Amsterdam, 1971, p. 79.
18. M. V. George, S. K. Khetan, R. K. Gupta, Adv. Heterocycl. Chem. 1976, 19, 279-371; R. K. Gupta, M. V. George, Tetrahedron 1975, 31, 1263-1275; W. E. Truce, G. J. V. Tichenor, J. Org. Chem. 1972, 37, 2391-2396.
19. M. V. George, S. K. Khetan, R. K. Gupta, Adv. Heterocycl. Chem. 1976, 19, 279-371; R. K. Gupta, M. V. George, Tetrahedron 1975, 31, 1263-1275; W. E. Truce, G. J. V. Tichenor, J. Org. Chem. 1972, 37, 2391-2396.
20. M. V. George, S. K. Khetan, R. K. Gupta, Adv. Heterocycl. Chem. 1976, 19, 279-371; R. K. Gupta, M. V. George, Tetrahedron 1975, 31, 1263-1275; W. E. Truce, G. J. V. Tichenor, J. Org. Chem. 1972, 37, 2391-2396.
21. D. A. Ben-Efraim in The Chemistry of the Carbon-Carbon Triple Bond (Ed.: S. Patai), Wiley-Interscience, New York, 1978, part 2, chapter 18.