No.140
Oxidizing Reagent
| A2065 | 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (1) |
5g |
1 is a convenient, stable, and recyclable oxidizing agent, particularly useful in oxidizing allylic alcohols, as in the synthesis of geranial 3 from geraniol 2,1) and the oxidation of hemiacetal 5, such as an aldose sugar, into aldonolactone 6.2) Byproduct 4 can be oxidized using sodium hypochlorite and recycled back into 1 for reuse. It can also be used to transform bifunctional alcohol 7 into ester 8 by oxidative dimerization3) and in the synthesis of allylic alkoxyamines.4)
References
1) A stable and convenient reagent for the oxidation of alcohols
J. M. Bobbitt, J. Org. Chem. 1998, 63, 9367[DOI]; J. M. Bobbitt, N. Merbouh, Org. Synth. 2005, 82, 80.
2) Oxidation of O-1 unprotected monosaccharides to lactones
N. Merbouh, J. M. Bobbitt, C. Brückner, Tetrahedron Lett. 2001, 42, 8793[DOI].
3) Oxidative dimerization of polyfunctional primary alcohols to esters
N. Merbouh, J. M. Bobbitt, C. Brückner, J. Org. Chem. 2004, 69, 5116[DOI].
4) Ene-like addition of an oxoammonium cation to alkenes
P. P. Pradhan, J. M. Bobbitt, W. F. Bailey, Org. Lett. 2006, 8, 5485[DOI].
J. M. Bobbitt, J. Org. Chem. 1998, 63, 9367[DOI]; J. M. Bobbitt, N. Merbouh, Org. Synth. 2005, 82, 80.
2) Oxidation of O-1 unprotected monosaccharides to lactones
N. Merbouh, J. M. Bobbitt, C. Brückner, Tetrahedron Lett. 2001, 42, 8793[DOI].
3) Oxidative dimerization of polyfunctional primary alcohols to esters
N. Merbouh, J. M. Bobbitt, C. Brückner, J. Org. Chem. 2004, 69, 5116[DOI].
4) Ene-like addition of an oxoammonium cation to alkenes
P. P. Pradhan, J. M. Bobbitt, W. F. Bailey, Org. Lett. 2006, 8, 5485[DOI].
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