T-Butyl methyl ketone

Fig. 7.3. Crystal structures of some lithium etiolates of ketones. (A) Unsolvated hexameric enolate of methyl t-butyl ketone (B) tetrahydrofuran solvate of tetramer of enolate of methyl r-butyl ketone (C) tetrahydrofuran solvate of tetramer of enolate of cyclopentanone (D) dimeric enolate of 3,3-dimethyl-4-(r-butyldimethylsiloxy)-2-pentanone. (Structural diagrams are reproduced from Refs. 66-69.) by permission of the American Chemical Society and Verlag Helvetica Chimica Acta AG.

The yields ranged from 55% for the mixture of enamines formed from morpholine and methylisopropyl ketone to 94% for the enamine formed from dimethylamine and methyl t-butyl ketone. The hindered ketone 2,5-dimethylcyclopentanone could be converted to an enamine, but the more hindered ketone, 2,6-di-t-butylcyclohexanone, was inert. White and Weingarten 43) attribute the effectiveness of titanium tetrachloride in this reaction to its ability to scavenge water and to polarize the carbonyl bond. 

Fig. 1.3. Potassium enolate of methyl t-butyl ketone open circles are oxygen and small circles are potassium, (a) left panel shows only the enolate structures (b) right panel shows only the solvating THF molecules. The actual structure is the superposition of both panels. Reproduced from J. Am. Chem. Soc., 108, 462 (1986), by permission of the American Chemical Society.

Methyl ketones lead to different triazoles, depending on the azide and ketone employed (Scheme 135).2 5 s Reaction of benzyl azide with acetone and acetophenone yields mostly one or both of the triazoles derived from 38 and 39 in Scheme 64. Methyl t-butyl ketone gives, in addition, a 4-triazenyl-... 

Fig. 6. The log Pmax 1/ plots for equimolar ketgne—oxygen mixtures [45]. Pm ax is the maximum rate of reaction in torr. min . (1) Methyl t-butyl ketone, F(total) = 300 torr (2) acetone, F(total) = 300 torr (3) diethyl ketone, F(total) = 65 torr.

Beilstein Handbook Reference) AI3-03075 BRN 1209331 t-Butyl methyl ketone tert-Butyl methyl ketone EINECS 200-9204 HSDB 5210 Ketone, t-butyl methyl Ketone, tert-butyl methyl Methyl t-butyl ketone Methyl tert-butyl ketone NSC 935 Pinacolin Pinacoline Pinacolone Pinakolin. Used in chemical synthesis, manufacture. Liquid mp = -52.5° bp = 106.1° d = 0.7229 slightly soluble in H2O (2.5 g/100 ml), more soluble in organic solvents LD50 (rat orl) = 610 mg/kg. Lancaster Synthesis Co. Mallinckrodt inc. Sigma-Aldrich Fine Chem. 

A study of the results of photolysis of methyl t-butyl ketone, di-t-butyl ketone, pivalaldehyde, and isobutyraldehyde by cidnp has been reported.1 Other workers... 

One such reaction is the acid-catalyzed conversion of diols to ketones. This reaction is sometimes referred to as the pinacol rearrangement. The classic example of the reaction is the conversion of 2,3-dimethylbutane-2,3-diol (pinacol) to methyl t-butyl ketone (pinacolone) ... 

A study of the mechanism of singlet-oxygen oxidation has focused on adaman-tylideneadamantane, A. The reaction gives the products shown when carried out in methyl t-butyl ketone as solvent. What relevance do these results have to the question of a perepoxide intermediate in singlet-oxygen oxidations ... 

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