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Trifluoromethyl phenyl sulfone

Solubility soluble in alcohols, ethers, CH2CI2, CHCI3, DMF, and DMSO. [Pg.604]

Form Supplied in colorless liquid often prepared by the oxidation of trifluoromethyl phenyl sulfide using aqueous hydrogen peroxide in acetic acid.  [Pg.604]

Handling, Storage, and Precautions PhS02Cp3 has high reactivity with bases and reducing metals store under anhydrous, neutral conditions use in a fume hood. [Pg.604]

Teruo Umemoto Daikin MFC Laboratory, Tsukuba, Japan [Pg.604]

The magnesium-mediated reductive trifluoromethylation also works for other structurally diverse chlorosilanes. Chlorotriethyl-silane, f-hutyldimethylsilyl chloride, and tris(trimethylsilyl)silyl chloride have been applied to prepare corresponding trifluoro-methyl-containing silanes. However, the reductive trifluoromethylation did not take place with other electrophiles such as aldehydes, ketones, allyl bromide, benzyl chloride, or tributyltin chloride. Even tributyltin hydride and allyltrimethylsilane showed no reactivity The reason for such behavior is not clear. Probably, chlorosilanes play an important role during the reductive trifluoromethylation both as a silylating agent and a single-electron transfer promoter. [Pg.604]


Other aryl sulfones that can accommodate the nucleophilic addition step also react in the same way. For example, excellent results have been obtained using 3,5-bis-(trifluoromethyl)phenyl sulfones.281... [Pg.175]

The reaction between a carbanion derived from alkyl 3,5-bis(trifluoromethyl)phenyl sulfones and aldehydes affords, with good yields and stereoselectivities, the corresponding 1,2-disubstituted alkene through the Julia-Kocienski olefination reaction. This one-pot protocol can be performed using the phosphazene base at —78 °C and has been successfully used in a high yielding and stereoselective synthesis of various stilbenes such as resveratrol [47] (Scheme 5.28). [Pg.162]

Scheme 19.18 3,5-Bis(trifluoromethyl)phenyl sulfones in Julia-Kocienski reactions. Scheme 19.18 3,5-Bis(trifluoromethyl)phenyl sulfones in Julia-Kocienski reactions.
Another application of trifluoromethyl phenyl sulfone is in the preparation of benzenesulfonic acid (or metal benzenesulfonate) using oxygen nucleophiles. Trifluoromethyl phenyl sulfone is readily transformed into benzenesufonate salt upon treatment with an alkoxide or hydroxide (eq 6). This is particularly useful for the convenient transformation of a polymer-supported trifluoromethyl phenyl sulfone into polymer-supported sulfonic acid (or sufonate) ion-conducting materials. " ... [Pg.605]

Prakash and co-workers have prepared monofluoro-methyl 3,5-bis(trifluoromethyl)phenyl sulfone and have used it in the fluoroalkenylation of aldehydes and ketones.They employ KOH or CsF as base in DMSO at 20°C. On their side, Hu and co-workers have developed TBTSO2CH2F as a versatile fluoromethylidene synthon. Difluoromethyl 2-pyridyl sulfone has been used for the gem-difluoromethylenation of aldehydes and ketones and was found to be a more efficient difluoromethyfidene synthon than BTSO2CF2H, PTSO2CF2H and TBTS02CF2H. ... [Pg.633]

Alonso DA, Fuensanta M, Najera C. 3,5-Bis(trifluoromethyl) phenyl sulfones in the Julia-Kocienski olefination-applica-tion to the synthesis of tri and tetrasubstituted olefins. Eur. J. Org. Chem. 2006 (20) 4747 754. [Pg.657]


See other pages where Trifluoromethyl phenyl sulfone is mentioned: [Pg.142]    [Pg.604]    [Pg.604]    [Pg.604]    [Pg.604]    [Pg.605]    [Pg.605]    [Pg.605]    [Pg.605]    [Pg.652]    [Pg.658]    [Pg.664]    [Pg.631]   
See also in sourсe #XX -- [ Pg.604 , Pg.605 ]




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