Reactivity of N-(hydroperoxyalkyl)nitrones towards dipolarophiles. Synthesis of some 2-(hydroperoxyalkyl)-2,3-dihydroisoxazoles

Synthesis

Volumn , Issue 3, 1998, Pages 333-338

  Iesce, M Rosaria ^a   Cermola, Flavio ^a   Guitto, Antonio ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

2 (hydroperoxyalkyl) 2,3 dihydroisoxazoles; Alkenes; Alkynes; N (hydroperoxyalkyl)nitrones; 3+2 cycloaddition

Indexed keywords

ISOXAZOLE DERIVATIVE; NITRIC ACID DERIVATIVE;

ARTICLE; COVALENT BOND; DECOMPOSITION; DRUG STABILITY; DRUG SYNTHESIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; THERMOREGULATION;

EID: 0031951194     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2040     Document Type: Article

References (24)

1. Iesce, M. R.; Cermola, F.; Guitto, A.; Giordano, F.; Scarpati, R. J. Org. Chem. 1996, 61, 8677.
2. 3
3. Freeman, J. P. Chem. Rev. 1983, 83, 241.
4. Iesce, M. R.; Cermola, F.; Guitto, A. Synthesis 1997, 657.
5. 6
6. Sims, J.; Houk, K. N. J. Am. Chem. Soc. 1973, 95, 5798.
7. Any excess of 2c is readily removed due to its low boiling point (76.5°C).
8. 2O.
9. Semiempirical calculations performed with AM1 method using the program Hyperchem 4.5 showed that the order of electrophilicity is 2b 7ap; 2c > 2a. On the other hand, the dienophile reactivity sequence also in the Diels-Alder reactions is dicyanoacetylene > dimethyl acetylenedicarboxylate see Aga, M.; Okada, K.; Oda, M. Tetrahedron Lett. 1986, 27, 5653.
10. Screening experiments showed that the other N-(hydroperoxyalkyl)nitrones 1 behave similarly.
11. 12 Taking this into account, the failure of cycloaddition of these alkenes to 1a can be rationalized.
12. Tufariello, J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 2, Chapter 9.
13. a) Lang Jr., S. A.; Lin, Y.-i In Comprehensive Heterocyclic Chemistry; Katritzsky, A. R.; Rees, C. W., Eds; Pergamon: Oxford, 1984, Vol. 6, 127.
14. b) Grünanger, P.; Vita-Finzi, P. Isoxazoles In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley-Interscience: New York, 1991; part I.
15. For hydroperoxide applications see among others: a) Oda, K.; Takei, K. Jpn. Patent 0710709, 1995;
16. Chem. Abstr. 1995, 122, 207776r.
17. b) Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992.
18. Sheldon, R. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983, p 161.
19. Kropf, H.; Torkler, F. In Houben-Weyl, 4th ed., Vol. E14b/2; Kropf, H. Ed.; Thieme: Stuttgart, 1990; p 39.
20. Lutz, R. E.; Smithey, W. R., Jr. J. Org. Chem. 1951, 16, 51.
21. Jäger, V. In Houben-Weyl, 4th ed., Vol.V/2a; Müller, E. Ed.; Thieme: Stuttgart, 1977; p 677.
22. McElvain, S. M.; Anthes, H. J.; Shapiro, S. H. J. Am. Chem. Soc. 1942, 64, 2525.
23. 19
24. Porter, N. A. In Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992, p 124.