Cetyltrimethylammonium permanganate

Oxidation of 9-(4-pyridylvinyl)-7-methyl-2-morphohno-4//-pyrido[l, 2-a -pyrimidin-4-one with cetyltrimethylammonium permanganate in CH2CI2 at room temperature for 5 h yielded a 9-formyl derivative (01MIP9). 

Secondary nitroalkanes are oxidized by cetyltrimethylammonium permanganate to yield ketones in moderate to good yield [44]. The reaction is sufficiently mild to leave double bonds and hydroxyl groups unaffected. 

Lead tetraacetate-Manganese(II) acetate, 157 Osmium tetroxide, 222 Potassium ruthenate, 259 Samarium(II) iodide, 270 reagents specific for primary alcohols Osmium tetroxide, 222 reagents specific for benzylic alcohols Cetyltrimethylammonium permanganate, 69... 

Potassium nitrosodisulfonate, 258 other methods Bis(tributyltin) oxide, 41 /-Butyl hydroperoxide-Dichlorotris-(triphenylphosphine)rutheni-um(II), 54 Dibutyltin oxide, 95 Hydrogen hexachloroplatinate(IV)-Copper(II) chloride, 145 4-Methoxy-2,2,6,6-tetramethy 1-1 -oxopiperidinium chloride, 183 of alcohols to carboxylic acids Cetyltrimethylammonium permanganate, 69... 

Vinylmagnesium bromide, 186 Manganese Compounds Bromopentacarbonylmanganese, 49 Butylmanganese(II) iodide, 210 Cetyltrimethylammonium permanganate, 69... 

Cetyltrimethylammonium permanganate (CTAP), a stable quaternary ammonium salt, provides a valuable modification of the original permanganate procedure for selective conversion of substrates containing alkenic and hydroxy groups. Yields are good to excellent (Scheme 44) and large quantities of substrate can be transformed. 

Kym, P. R., Wilson, S. R., Gritton, W. H., Katzenellenbogen, J. A. Novel steroids from cetyltrimethylammonium permanganate-initiated oxidative rearrangements of 16-dehydroprogesterone. Tetrahedron Lett. 1994, 35, 2833-2836. 

Mallya, M. N., Nagendrappa, G. cis-Hydroxylation of cyclic vinylsilanes using cetyltrimethylammonium permanganate. Synthesis 1999, 37-39. 

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