Trifluoromethyl carbinol

Table 14. NMR Data for Trifluoromethyl Ketones and Corresponding Trifluoromethyl Carbinols...

As an example, bis(trifluoromethyl) carbinols have been described as strong inhibitors of malonyl-CoA decarboxylase, an enzyme involved in the metabolism of fatty acids, a possible target for the treatment of ischemic heart disease and diabetes (Figure 7.24)." Although few enzymological data are available, it is reasonable to... 

Table 12 [19,56,101,102,103], Table 13 [56, 73,104], and Table 14 [56,105, 106] cover six common CFj-containing subunits of general interest and utility tnfluoroethanes, trifluoroacetates, tnfluoroacetanudes, tnfluoromethanesulfon-ates, trifluoromethyl ketones, and trifluoromethyl carbinols. The majority of these data were acquired under uniform conditions (10% solutions in CDC13 at room temperature [56]) to provide for a valid comparison of 19F-NMR values within a narrow range of approximately 10 ppm. Most of these compounds are common,... 

Radical copolymerizadon of substituted norbomenes mth sulfur dioxide produced alternating copolymers in excellent yields in a few hours. The copolymers had an OD of 0.25-0.33/pm at 193 nm. The acidic di(trifluoromethyl)carbinol structure incorporated into the poly(norbomene sulfone) provided an extremely fast dissolution rate in aqueous base. Terpolymerization with carbo-/>butoxynorbomene resulted in an exponential decay of the ssolution rate. In contrast to poly(styrene sulfones), however, poly(norbomene sulfones) exhibited unacceptably fast etching in... 

Sonication. Ultrasonic radiation was introduced in Zn-Barbier chemistry in 1981 [68], soon after it was applied for the first time in organometallic chemistry [32] for Li-Barbier reactions iodotrifluoromethane was reacted with commercially available zinc (no mention was made of any activation of the metal) in the presence of an aldehyde or a ketone in DMF or THF to give the expected trifluoromethyl carbinols in reasonable yields (50-70%). 

Reactions with Carbonyl Compounds. TMSCF3 reacts with aldehydes in the presence of a catalytic amount of tetra-w-butylammonium fluoride (TBAF) in THF to form the corresponding trifluoromethylated carbinols in good to excellent yields following aqueous hydrolysis of the silyl ethers (eq 3) 2.3.6,10 The reaction also works very well for ketones under the same conditions, with the exception of extremely hindered ones such as l,7,7-trimethylbicyclo[2.2.1]heptan-2-one, di-l-adamantyl ketone, and fenchone. The reaction has been characterized as a fluorideinduced autocatalytic reaction. Other initiators such as tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF), potassium fluoride, Ph3SnF2, andRO can also be used for these reactions. ForthereactionsofTMSCFs and perfluorinated ketones and pentafluorobenzaldehyde, excess of KF is needed. 

The ting cleavage reactions of the triflumomethyloxirane with die appropriate nucleophiles provided a general synthesis of chiral trifluoromethyl carbinols, such as 1-amino-3,3>3-trifluoro-2-propanol, l-azido-3,3.3-tiifluoro-2-propanol, 1-diediylamino-... 

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