1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane Periodate: a Mild and Efficient Oxidant for the Cleavage of Oxime Double Bonds under Anhydrous Conditions†

Abstract

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate (BAABCP) (1), readily prepared from commercially available 1,4-diazabicyclo[2.2.2]octane (DABCO) and sodium periodate, converts oximes and α-sulfinyl oximes to the corresponding carbonyl compounds and β-keto sulfoxides, respectively, in high yields and high enantiomeric purity.

References

1. E. B. Hersberg, J. Org. Chem., 1948, 12, 541.
2. C. G. Rao, A. S. Radhakrishna, B. B. Singh and S. P. Bhatnagar, Synthesis, 1983, 808.
3. S. Satish and N. Kalyanam, Chem. Ind. (London), 1981, 809.
4. S. H. Pines, J. M. Chemerda and M. A. Kozlowski, J. Org. Chem., 1966, 31, 3446.
5. J. Drabowicz, Synthesis, 1980, 125.
6. S. G. Pyne and A. R. Hajipour, Tetrahedron, 1994, 50, 13 501.
7. G. Solladie, G. Demaily and C. Greck, Tetrahedron Lett., 1985, 26, 435.
8. (a) R. Annunziata and M. Cinquini, Synthesis, 1982, 929; (b) A. R. Hajipour; S. G. Pyne, unpublished results.
9. Catalogue Handbook of Fine Chemicals, Aldrich, 1992.
10. R. Annunzian, M. Cinquini and F. Cozzi, J. Chem. Soc., Perkin Trans. 1, 1979, 1689.
11. G. Solladie, G. Demilly and C. Greck, J. Org. Chem., 1985, 50, 1552.
12. F. A. Carey and O. Hernandez, J. Org. Chem., 1973, 38, 2670.
13. L. Banfi, L. Colombo and C. Gennari, Synthesis, 1982, 829.