NMR Studies and Crystal Structure Determinations of CF₃ Group-containing Bicyclic Phenolates

Abstract

Three new CF 3 -substituted bicyclic salicylate derivatives were synthesized by the TiCl 4 -mediated cyclization of trifluoromethyl-containing ketones with 1,3-bis(silyl enol ethers) and characterized by NMR and IR, spectroscopy, mass spectrometry and elemental analysis. The crystal structures of the bicyclic derivatives have been determined by single crystal X-ray analysis. All structures exhibit hydrogen bonding.

A solvent-free, base-catalyzed domino reaction towards trifluoromethylated benzenes from bio-based methyl coumalate

“…This is consistent with an aromatic CF 3 moiety. 22 The putative trifluoro-acetophenone regioisomer derivative would have its COCF 3 signal shifted up-field at around -70, -80 ppm. The effect of the substituent on the aromatic ring was investigated.…”

Heterocyclizations of β-alkoxy, β-diaminoalkyl, and related β-functionalized enones (enals) with NCN-binucleophiles

“…To address the above issues, β-alkoxyvinyland β-enaminocarbonyl compounds have been developed as the synthetic equivalents of classical 1,3-dicarbonyl CCC bis-electrophiles with a push-pull reactivity (Scheme 1). In addition to increased stability and the possibility to synthesize the simplest and the least substituted functionalized heterocycles [11][12][13][14][15], these building blocks provide increased chemo-and regioselectivity with diminished side processes, as well as improved yields of the condensation product [16][17][18][19][20][21][22][23]. The synthesis of these biselectrophiles can be achieved starting from 1,3-dicarbonyl compounds [16,[24][25][26] or alkoxyvinyl acetylenes [27], by reaction of ketals with acylating agents [28,29], acylation of vinyl ethers [29][30][31], the Heck-type palladium-catalyzed carbonylation of vinyl ethers in the presence of aryl iodides and carbon monoxide [32,33], and other methods.…”