Ketones, mesityl phenyl

Ashby, E. C., Boone, J. R., Mechanism of Lithium Aluminum Hydride Reduction of Ketones. Kinetics of Reduction of Mesityl Phenyl Ketone, J. Am. Chem. Soc. 1976, 98, 5524 5531. 

Mesityl phenyl ketone Mesityl (phenyl) methanone. See 2,4,6-Trimethylbenzophenone Mesobenzanthrone. See Benzanthrone, meso-2,3-Dimethyl-2,3-butanediol. See Pinacol meso-Erythritol. See Erythritol meso-lnositol. See Inositol meso-lnositol hexanicotinate. See,Inositol hexanicotinate... 

Trimethylbenzol. See 1,3,5-Trimethylbenzene 2,4,6-Trimethylbenzophenone CAS 954-16-5 EINECS/ELINCS 403-150-9 Synonyms Benzophenone, 2,4,6-trimethyl- Ketone, mesityl phenyl Mesitylene, 2-benzoyl- Mesityl phenyl ketone Mesityl (phenyl) methanone... 

The first conjugate addition reaction to be observed in this series was with mesityl phenyl ketone and the phenyl reagent. The product, obtained in a yield of 18%, was 2-mesitoylbiphenyl (29). 

Bode and co-workers further extended redox esterification to include carbon-carbon bond breaking of formyl-cyclopropanes [113]. Both esters and thioesters are formed in high yield and good enantioselectivities (Scheme 31). The M-mesityl substituted triazolium salt 191 proved to be the most efficient pre-catalyst providing complete suppression of the benzoin reaction. Electron-deficient substituents, such as phenyl ketone, readily provide ester formation. 

Ketone, ethyl vinyl. See Ethyl vinyl ketone Ketone, 2-furyl methyl. See 2-Acetylfuran Ketone, o-hydroxybenzyl phenyl. See Benzoin Ketone, mesityl phenyl. See 2,4,6-T ri methylbenzophenone Ketone, methyl isoamyl. See Methyl isoamyl ketone... 

Highly enantioselective hydrosilylation of aliphatic and aromatic carbonyl compounds such as acetophenone, methyl phenethyl ketone 1813, or deuterobenz-aldehyde 1815 can be readily achieved with stericaUy hindered silanes such as o-tolyl2SiH2 or phenyl mesityl silane 1810 in the presence of the rhodium-ferrocene catalyst 1811 to give alcohols such as 1812, 1814, and 1816 in high chemical and optical yield [47] (Scheme 12.14). More recently, hydrosilylations of aldehydes... 

The reduction of phenyl mesityl ketone was studied with LAH modified with amino alcohols 65 to 72 in ether (the ratio LAH alcohol ketone = 1.1 1.1 1) (83). Optical yields were modest, with the highest 39%, obtained with 65 as the chiral auxiliary reagent. It was observed that there is a relationship between the preferred enantiomeric product and the structure and absolute configuration of the carbons carrying the hydroxy and amino groups. Thus the threo... 

A number of ,(8-unsaturated ketones 227 270-272 and (8-halo-ketones227, 270 have been condensed with o-phenylenediamine to give diazepines (225, R4 = H). Use of V-phenyl-o-phenylenediamine gave 225 (R = C6H5) and 226.270 The reaction of mesityl oxide with o-phenylenediamine had been reported273 to give a benzimidazole however, investigation of the product by NMR indicates that it has structure 225 (R1 = R2 = R3 = CH3, R4 = H).274... 

The advantage of using a catalyst is obvious. When one reactive center of the keto compound is substituted by a methyl or phenyl group (Rz) the catalyst effect is more enhanced. Mesityl oxide (Rj = Rz = R3 = Me) requires very high pressure and efhcient lanthanide catalysis. This reaction involving a sterically congested unsaturated ketone is a prominent example emphasizing the requirement of biactivation to overcome steric hindrance. It should be added that, apart from the mesityl oxide reaction, a modest pressure (300 MPa) is sufficient to induce reactivity in these catalyzed reactions which were shown to proceed only at pressures in excess of 1200 MPa in an uncatalyzed version [33]. 

Unsaturated acids can also be obtained in this way, by hypohalite oxidation of a,/ -unsaturated methyl ketones 3-methyl-2-butenoic acid has thus been obtained from mesityl oxide,136 and 5-phenyl-2,4-pentadienoic acid in 70% yield from cinnamylideneacetone 137... 

The procedure involves reaction in acetic anhydride, or in another solvent, followed by the addition of acetic anhydride to decompose the intermediate complex. The procedure has been extensively examined in relation to the 5-methyl- and 4,5-dimethyl-substituted compounds derived from ethenyl methyl and methyl isopropenyl ketones and with mesityl oxide which gives the 3,3,5-trimethyl-substituted compounds. Amongest the phosphorus reactants, the trichloride itself and methyl- " , ethyl- " " and phenyl- phosphonous dichlorides have been employed, as have ethyl and phenyP dichlorophosphites, ROPCI2. The use of 2-thienylphosphonous dichloride to give 137 is recorded as is that of the unsaturated ketone 138 to give 139. A more novel conversion is that of 140 into 141 in 25% yield with a similar conversion (15%) being observed for cholest-4-en-3-one. ... 

Furstner indole synthesis is not necessarily performed in a two-step fashion, instead it can be efficiently carried out via an instant method. Under such conditions, TiCb is added to form a complex with oxoamide substrates before the addition of an excess amount of zinc once TiCb is reduced to an active oxidation state, it immediately mediates the alkylidenation of two adjacent carbonyl functionalities. Furthermore, unlike McMurry Coupling, the Furstner indole synthesis is not restricted to THF or DME, it can also be performed in solvents such as EtOAc, DMF, and CH3CN, although it does not work in toluene and MeOH. What is more, a variety of reducible and acid or base-labile functionalities at other sites of the substrates can sustain the Eiirstner indole synthesis. Eor example, 2-N-o -ketoacylamidophenyl ketone with a more electrophilic a-keto group cyclizes only to a indole derivative. In addition, a pair of phenyl/mesityl or benzyl/t rt-butyl groups at C-2 and C-3 in either possible arrangement does not affect the overall yield of indole derivatives to a noticeable extent. ... 

Assignment based on radical obtained from /g-phenyl mesityl ketone. 

Among the other simple compounds reduced by diphenyltin dihydride are cyclohexanone (82%), benzaldehyde (62%), mesityl oxide (60%), and chalcone (75%). It can be seen that the yields are high with the simple ketones and aldehydes, and moderate in the case of the a,]8-unsaturated analogs. The cause of the lower yields has not been examined, but may be due to the occurrence of hydrostannation, particularly of the product alcohol, as a side reaction. In all of these cases the unsaturated alcohol was the reduction product the double bond was not reduced. The same is true when triphenyltin hydride is used in the reduction of methyl vinyl ketone and phenyl vinyl ketone 66). 

A similar condensation was realized with mesityl 1-naphthyl ketone and the phenyl reagent. The intermediate formation of the enol was demonstrated in the condensation of methylmagnesium iodide with mesityl 2-naphthyl ketone the hydroperoxide was obtained in a yield of 74% (JO). 

Phenanthryl mesityl ketone was found to react in the 1,4-manner with the methyl and phenyl reagents 32). 

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