Tri fluoroacetamide

ALmethyl-/V-( triinethylsilyl)-tri-fluoroacetamide 6971 methyl (triphenylphosphoranylidene)-acetate 553 methyl homosecodaphni-phyllate 465 ff. 

Gas chromatographic separation of amphenicols is further complicated by the need for derivatization of their polar functional groups. Silyl derivatives formed by treating sample extracts with N,O-bis(trimethylsilyl)acetamide (49), trimethylsilyl N,N-dimethyl carbamate (47), N,O-bis(trimethylsilyl)tri-fluoroacetamide/trimethylchlorosilane (99 1) mixture (32, 51), or mixture of... 

Panek et al. employed the optically active amines 252 and 254 [57]. Their condensation with various aldehydes in the presence of MgS04 probably afforded the corresponding imines, which were treated with TiCl4. The resulting substituted 1,2,5,6-tetrahydro pyridines were finally protected, affording the corresponding tri-fluoroacetamides 253 and 255. In all cases, the desired tetrahydropyridines 253 and 255 could be isolated in excellent yields. The IMSC condensation also displays a high diastereoselectivity (Scheme 13.93). 

After evaporation to dryness the fractions are derivatized by heating with bis-trimethylsilyl tri-fluoroacetamide (BSFTA) at 90°C for one hour. 

Removal of the endo methylene bridge of Troger s bases could be achieved with or without concomitant methylation of the nitrogen(s). Thus, trifluoroacetylation of 215b with trifluoroacetic anhydride did not give the expected bis(tri-fluoroacetamide) 217 (R1 = R2 = CF3CO) but rather the trifluoroacetamide trifluoroacetate salt 216 in 79% yield. 

Modified Curtius rearrangement. Acyl azides, preferably prepared in situ under phase-transfer conditions by reaction of acid chlorides and NaN, are converted to tri-fluoroacetamides by reaction with CF,COOH in refluxing CH CI, solution. These products are cleaved to primary amines under mild conditions (equation I). ... 

Under certain conditions the reduction of amides leads to primary alcohols (cf. method 428). Thus, phenylethylacetamide is reduced by sodium and absolute ethanol to 2-phenyl-1-butanol (75%). a-Naphthylacetamide is reduced by sodium amalgam and hydrochloric acid to a-naphthylcarbinol (63%). Trifluoroethanol is obtained by catalytic hydrogenation of tri-fluoroacetamide over a platinum catalyst. Hydrogenation of the corresponding ester over copper-chromium oxide failed. ... 

Dimethyl-fert-butylsilyl tri fluoroacetamide MTBSTFA 241 168-170 996 13" CF3CONH2 (675 11)... 

---