Isophorone oxide, reduction

Reduction of a, ji-epoxy ketones with NaHTe (typical procedure) ji-Epoxy ketonesP To a solution of NaHTe (prepared from Te (1.30 g, 10 mmol) and NaBH (0.90 g, 0.24 mmol)) in EtOH is added isophorone oxide (0.616 g, 4 mmol) in EtOH (4 mL). An instantaneous... 

Environmental Fate. Sensitized photolysis studies in water and oxidation/reduction studies in both air and water are lacking, as are biodegradation studies in surface and groundwaters. These kinds of studies are important, since they represent the fundamental removal mechanisms available to isophorone in the environment. In addition, the kinetic studies for the atmospheric reactions are important for understanding the significance of a removal mechanism and predicting the reactions that may control the fate of a chemical in the environment. 

Further reactions on these compounds lead to other oxidised products in which the lack of stereochemical control in the epoxidation is unimportant, so, for example isophorone oxide rearranges with various catalysts to the cyclopentanone 182 (80% yield) while both isomers of pulegone oxide 179 gives the cycloheptadione29 183 (78% yield). Exhaustive methylation of the extended enolate produced by reduction of 181 gives 184 in good yield.28... 

Researchers from BASF developed the Mn(II)-salen- or [Mn(ni)-salen]X-catalysed oxidation of y6-isophorone using salen derivatives with electron-withdrawing substituents without or in the presence of acetates as additives. The increase of ignition temperature of the hase/solvent mixture (ignition point of triethylamine/cUglyme 0°C) and thus a reduction of the explosion risk, was successfully achieved using tripropylamine in dimethylformamide (DMF) or dimethyl acetamide (DMA). With a chloro-substituted [Mn(in)-salen]Cl catalyst in the presence of Uthium acetate and tripropylamine in DMA, KIP was obtained in an 89.4% yield with minor amounts of by-products (1.5% a-isophorone, 1.3% hydroxy-isophorone) (Fig. 16.14). 

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