Ketones isophorone

Noteworthy features of these reactions are the high predominance of E stereochemistry in the case of aldehydes and the good results obtained even with highly enolizable ketones (such as cyclopentanone), a, -epoxy ketones (isophorone oxide) and a,j8-unsaturated compounds (benzalacetophenone and cinnamaldehyde). 

Extending their earlier work on Vilsmeier formylation (c/. Vol. 7, p. 36), Traas et al. have formylated the a/S-unsaturated ketone isophorone almost exclusively at the more favoured exocyclic position to yield (190), which may be selectively... 

Ketones Acetone Camphor Oil Cyclohexanone Diisobutyl Ketone Isophorone Mesityl Oxide Methyl Ethyl Ketone Methyl Isobutyl Ketone... 

Properties Solid. Mp 86C. Insoluble in water soluble in pine oil, diisobutyl ketone, isophorone, and xylene. Combustible. 

Acetone is used as a solvent for cellulose acetate, nitrocellulose and acetylene as a raw material for the chemical synthesis of such products as ketones, acetic anhydride, methyl methacrylate, bisphenol-A, diacetone alcohol, methyl isobutyl ketone, isophorone, etc. 

Ketones are a class of functional groups that contain an internal carbonyl (C=0) group and are connected to two alkyl groups. In contrast, aldehydes are a class of functional groups that contain an external carbonyl group, attatched to alkyl substituent and a hydrogen. Examples of ketones are acetone, cyclohexanone, diacetone alcohol, diisobutyl ketone, isophorone, methyl amyl ketone, methyl ethyl ketone (MEK), methyl isoamyl ketone, methyl isobutyl ketone, and methyl propyl ketone. The general form of a ketone is as follows ... 

Conjugate Addition. Reagent (1) in THE adds in 1,2-fashion to Q , -unsaturated ketones, whereas in THF/HMPA, 1,4-addition is observed as result of kinetic control (eq 4) The hindered Q , -unsaturated ketone isophorone gave smooth 1,2-addition in THE (89%), while in THF/HMPA, 1,2- and 1,4-addition occurred (1 1) in low conversion. 1,2-Addition of (1) to acrolein afforded a building block for bongkrekic acid. 1,4-Addition of (1) to j" -(dienyl)Fe(CO)3 substituted alkylidene malonates is highly stereoselective. ... 

Methyl ethyl ketone Methyl isobutyl ketone Isophorone Cyclohexanone Other solvents Propylene oxide Toluol Xylol... 

Isophorone. Isophorone (3,5,5-trimethyl-2-cyclohexen-l-one) is a cycHc a,P-unsaturated ketone derived from the trimeri2ation of acetone. It has a light yellow color and a disagreeable camphoraceous odor. It has the tendency to discolor and form residues on prolonged storage. Isophorone is completely miscible with organic solvents, and other physical properties are Hsted ia Table 1. 

Isophorone usually contains 2—5% of the isomer P-isophorone [471-01-2] (3,5,5-trimethyl-3-cyclohexen-l-one). The term a-isophorone is sometimes used ia referring to the a,P-unsaturated ketone, whereas P-isophorone connotes the unconjugated derivative. P-lsophorone (bp 186°C) is lower boiling than isophorone and can be converted to isophorone by distilling at reduced pressure ia the presence of -toluenesulfonic acid (188). Isophorone can be converted to P-isophorone by treatment with adipic acid (189) or H on(Ill) acetylacetoate (190). P-lsophorone can also be prepared from 4-bromoisophorone by reduction with chromous acetate (191). P-lsophorone can be used as an iatermediate ia the synthesis of carotenoids (192). 

Palladium(II) acetate was found to be a good catalyst for such cyclopropanations with ethyl diazoacetate (Scheme 19) by analogy with the same transformation using diazomethane (see Sect. 2.1). The best yields were obtained with monosubstituted alkenes such as acrylic esters and methyl vinyl ketone (64-85 %), whereas they dropped to 10-30% for a,p-unsaturated carbonyl compounds bearing alkyl groups in a- or p-position such as ethyl crotonate, isophorone and methyl methacrylate 141). In none of these reactions was formation of carbene dimers observed. 7>ms-benzalaceto-phenone was cyclopropanated stereospecifically in about 50% yield PdCl2 and palladium(II) acetylacetonate were less efficient catalysts 34 >. Diazoketones may be used instead of diazoesters, as the cyclopropanation of acrylonitrile by diazoacenaph-thenone/Pd(OAc)2 (75 % yield) shows142). 

Selective 1,4-reduction of unsaturated aldehydes and ketones by 6 occurs smoothly in THF between —25 °C and room temperature within a few hours (Eq. 5.7). Particularly noteworthy is the realization that phosphines are noticeably absent from the reaction medium. The analogous combination of CuCl/BusSnH in N-methyl-2-pyrrolidinone (NMP) or DMF does not behave identically [22], failing to react with the hindered substrate isophorone, whereas a 72% yield of the corresponding reduced ketone is formed with reagents XCu(H)Li/Bu3SnH. Nonetheless, a form of CuH is being generated in this more polar medium, effectively utilized by Tanaka to arrive at 3-norcephalosporin 8 upon reaction with allenic ester 7 (Scheme 5.3). 

Indenopyrene, see Indeno[l,2,3-crf pyrene l//-Indole, see Indole Indolene, see Indoline Inexit, see Lindane Inhibisol, see 1,1,1-Trichloroethane Insecticide 497, see Dieldrin Insecticide 4049, see Malathion Insectophene, see a-Endosulfan, p-Endosulfan Intox 8, see Chlordane Inverton 245, see 2,4,5-T lodomethane, see Methyl iodide IP, see Indeno[l,2,3-crf pyrene IP3, see Isoamyl alcohol Ipaner, see 2,4-D IPE, see Isopropyl ether IPH, see Phenol Ipersan, see Trifluralin Iphanon, see Camphor Isceon 11, see Trichlorofluoromethane Isceon 122, see Dichlorodifluoromethane Iscobrome, see Methyl bromide Iscobrome D, see Ethylene dibromide Isoacetophorone, see Isophorone a-Isoamylene, see 3-Methyl-l-butene Isoamyl ethanoate, see Isoamyl acetate Isoamylhydride, see 2-Methylbutane Isoamylol, see Isoamyl alcohol Isobac, see 2,4-Dichlorophenol Isobenzofuran-l,3-dione, see Phthalic anhydride 1,3-Isobenzofurandione, see Phthalic anhydride IsoBuAc, see Isobutyl acetate IsoBuBz, see Isobutylbenzene Isobutane, see 2-Methylpropane Isobutanol, see Isobutyl alcohol Isobutene, see 2-Methylpropene Isobutenyl methyl ketone, see Mesityl oxide Isobutyl carbinol, see Isoamyl alcohol Isobutylene, see 2-Methylpropene Isobutylethylene, see 4-Methyl-l-pentene Isobutyl ketone, see Diisobutyl ketone Isobutyl methyl ketone, see 4-Methyl-2-pentanone Isobutyltrimethylmethane, see 2,2,4-Trimethylpentane Isocumene, see Propylbenzene Isocyanatomethane, see Methyl isocyanate Isocyanic acid, methyl ester, see Methyl isocyanate Isocyanic acid, methylphenylene ester, see 2,4-Toluene-diisocyanate... 

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... 

O Donoghue JL, Flaworth SR, Curren RD, et al. 1988. Mutagenicity studies on ketone solvents Methyl ethyl ketone, methyl isobutyl ketone, and isophorone. Mutat Res 206 149-161. 

One of the most thoroughly investigated aldol condensations is the selfcondensation of acetone. This is an important industrial reaction for the production of diacetone alcohol (DA) (Scheme 11), which is valuable as a chloride-free solvent and an intermediate in the synthesis of industrially important products such as mesityl oxide (MO), isophorone, methyl isobutyl ketone, and 3,5-xylenol. The reaction is exothermic, with the yield of DA decreasing with increasing reaction temperature it is usually performed with NaOH or KOH as a basic catalyst 118). 

Isobutane under Alkanes and Cyclic Aikanes Isobutyl Alcohol under Secondary Alcohols Isophorone under Ketones... 

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