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BIOLOGICAL INFO
Solubility:
Soluble in water
REVIEW Mild, selective oxidant for alcohols to aldehydes or ketones: Tetrahedron Lett., 2647 (1975); review: Synthesis, 245 (1982). Superior results have been reported with a catalytic amount of acetic acid: Tetrahedron, 46, 4417 (1990). Adsorption of the reagent onto alumina simplifies work-up and enhances reactivity in hydrocarbon solvents: Synthesis, 223 (1980). Improved results have also been obtained in the presence of silica gel, where reaction times are shortened by sonication: J. Org. Chem., 54, 5387 (1989). Oxidation of methylarenes to benzaldehydes has been reported. Selective mono-oxidation of xylenes to tolualdehydes can be achieved: Synlett, 2769 (2005).
REFERENCES
[1]
18-crown-6 complexes of chlorochromates as mild, selective oxidants: J. Org. Chem., 60, 2267 (1995).
[2]
Trialkyl boranes are also oxidized to carbonyl compounds, non-terminal boranes giving ketones: J. Organomet. Chem., 162, C9 (1978) and terminal boranes giving aldehydes: J. Organomet. Chem., 172, C20 (1979). Similarly, aldehydes can be prepared from terminal alkenes by oxidation of their adducts with thexylborane: Synthesis, 151 (1980).
[3]
In THF, arylhydroxylamines are selectively oxidized to nitroso compounds: Synth. Commun., 22, 1683 (1992).
[4]
For a brief feature on novel oxidation reactions with this reagent: Synlett, 741 (2003).
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