Fragmentation of chloroperoxides: Hypochlorite-mediated dehydration of hydroperoxyacetals to esters

Tetrahedron Letters

Volumn 51, Issue 42, 2010, Pages 5615-5617

  Fisher, Thomas J ^a   Dussault, Patrick H ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

Chloroperoxide; Ester; Fragmentation; Hydroperoxyacetal; Hypochlorite

Indexed keywords

ACETAL DERIVATIVE; CHLOROPEROXIDE DERIVATIVE; ESTER; HYDROPEROXYACETAL DERIVATIVE; HYPOCHLORITE; PEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DESICCATION; FRAGMENTATION REACTION; ONE POT SYNTHESIS; OZONOLYSIS; QUANTUM YIELD; REACTION ANALYSIS; STOICHIOMETRY;

EID: 77956648179     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.068     Document Type: Article

References (34)

1. K. Zmitek, M. Zupan, and J. Iskra Org. Biomol. Chem. 5 2007 3895 (α-oxygenated hydroperoxides, transacetalization)
2. A. Scarso, and G. Strukul A. Berkessel, Science of Synthesis Vol. 38 2009 Thieme Stuggart 36 52 (trapping of carbonyl oxides)
3. P.H. Dussault C.S. Foote, J.S. Valentine, A. Greenberg, J.F. Liebman, Active Oxygen in Chemistry 1995 Blackie A&P London 141 203 (addition to enol ethers)
4. P.H. Dussault, I.Q. Lee, H.J. Lee, R.J. Lee, Q.J. Niu, J.A. Schultz, and U. Zope J. Org. Chem. 65 2000 8407 (photooxygenation of enol ethers)
5. S.K. Ivanov, and H. Kropf H. Kropf, Methoden der Organischen Chemie Vol. E13 4th ed. 1988 Thieme Stuttgart 1031 1037
6. R. Criegee Liebigs Ann. 560 1948 127
7. H. Kropf H. Kropf, Methoden der Organischen Chemie Vol. E13 4th ed. 1988 Thieme Stuttgart 1095 1099
8. R.M. Ellam, and J.M. Padbury J. Chem. Soc., Chem. Commun. 1972 1086
9. Base-promoted fragmentation of hydroperoxyacetals is likely involved in a direct ozonolytic conversion of terminal alkenes to methyl esters: J.A. Marshall, and A.W. Garofalo J. Org. Chem. 58 1993 3675
10. G. Evano J.S. Panek, Science of Synthesis Vol. 20b 2007 Thieme Stuttgart 795 797
11. Q.E. Thompson J. Org. Chem. 27 1962 4498
12. R.E. Claus, and S.L. Schreiber Org. Synth. 64 1986 150
13. C. Schwartz, J. Raible, K. Mott, and P.H. Dussault Tetrahedron 62 2006 10747
14. 2, and water.
15. 2 and the filtrate is concentrated.
16. M.J. Mintz, and C. Walling Org. Synth. 49 1969 9
17. 3CN (1 mL) and added in one portion via syringe. The reaction is stirred vigorously for 10 min and then worked up as before.
18. Prepared by Ag(I)-mediated displacement: P.G. Cookson, A.G. Davies, and B.P. Roberts J. Chem. Soc., Chem. Commun. 1976 1022
19. A.N. Osipov, O.M. Panasenko, A.V. Chekanov, and J. Arnhold Free Radical Res. 36 2002 749
20. P. Marwah, A. Marwah, and H.A. Lardy Green Chem. 6 2004 570
21. M. Ochiai, T. Ito, H. Takahashi, A. Nakanishi, M. Toyonari, T. Suleda, S. Goto, and M. Shiro J. Am. Chem. Soc. 118 1996 7716
22. N.A. Milas, and B. Plesnicar J. Am. Chem. Soc. 90 1968 4450
23. 11/s for the unsubstituted 2-phenylcyclopropyl methyl radical: M.H.L. TadicBiadatti, and M. Newcomb J. Chem. Soc., Perkin Trans. 2 1996 1467
24. 2 to dihydropyran: N.A. Milas, R.L. Peeler Jr., and O.L. Mageli J. Am. Chem. Soc. 76 1954 2322
25. β-Scission of oxygenated alkoxy radicals: J.J. Orlando, G.S. Tyndall, and T.J. Wallington Chem. Rev. 103 2003 4657
26. S. Erhardt, S.A. Macgregor, K.J. McCullough, K. Savill, and B.J. Taylor Org. Lett. 9 2007 5569
27. H. Hock, and H. Kropf Angew. Chem. 69 1957 313
28. P.H. Dussault, H.J. Lee, and X. Liu Perkin. 1 2000 3006
29. M. Ochiai, A. Yoshimura, K. Miyamoto, S. Hayashi, and W. Nakanishi J. Am. Chem. Soc. 132 2010 9236
30. Chlorine test strips revealed the diluted aqueous layer from stoichometric reactions to have up to 50-60% of the theoretical amount of active chlorine.
31. M. Schnell, M. Mühlhäuser, and S.D. Peyerimhoff J. Phys. Chem. A 108 2004 1298
32. L.A. Medard Accidental Explosions: Types of Explosive Substances Vol. 2 1989 Ellis Horwood Ltd Chichester
33. P.A. Patnaik Comprehensive Guide to the Hazardous Properties of Chemical Substances 3rd ed. 2007 John Wiley and Sons Hoboken, NJ
34. J. Zabicky Z. Rappoport, The Chemistry of the Peroxide Group Vol. 2 2006 John Wiley and Sons Chichester 597 773 pt 2