V. I. Dyachenko

Synthesis of α-(4-hydroxyphenyl)-β,β,β-trifluoro-α-alanine derivatives

Abstract2,6-Dimethyl- and 2,6-dimethoxy-α-methoxycarbonyl-α-trifluoromethyl-p-methylenequinones have been synthesized. These compounds easily react with ammonia, morpholine, andp-toluidine to afford the corresponding α-(4-hydroxyphenyl)-β,β,β-trifluoro-α-alanine derivatives.

Reaction of hexafluoroacetone with sodium p-cresolate

Usually phenol and mono- and dialkylphenols C-alkylate polyfluoro ketones under drastic conditions (100-150/sup 0/C) with electrophilic catalysis. The authors have shown that sodium p-cresolate reacts slowly with hexafluoroacetone in nonpolar media at 20/sup 0/ and rapidly at 80/sup 0/C in the absence of a catalyst; here the mono- or di-C-alkylation product 2-(..cap alpha..-Hydroxyhexafluoroisopropyl)-4-methylphenol (I) or 2,6-Di(..cap alpha..-hydroxyhexafluoroisopropyl)-4-methylphenol (II) is formed, depending on the ratio of the reagents. The structure was established by /sup 1/H, /sup 13/C, and /sup 19/F NMR spectroscopy. The spectra were recorded in acetone on a Bruker WP-200 SY spectrometer at 200.13, 50.31, and 188.31 MHz respectively. The chemical shifts were determined with reference to TMS as internal standard and trifluoroacetic acid as external standard.