Phase transfer catalysis nucleophilic aromatic substitutions

Perchloro-organic chemistry structure, spectroscopy and reaction pathways, 25, 267 Permutational isomerization of pentavalent phosphorus compounds, 9, 25 Phase-transfer catalysis by quaternary ammonium salts, 15, 267 Phosphate esters, mechanism and catalysis of nucleophilic substitution in, 25, 99 Phosphorus compounds, pentavalent, turnstile rearrangement and pseudorotation in permutational isomerization, 9, 25 Photochemistry of aryl halides and related compounds, 20, 191 Photochemistry of carbonium ions, 9, 129 Photosubstitution, nucleophilic aromatic, 11, 225... 

The first comprehensive study applying phase transfer catalysis to aromatic nucleophilic substitution appeared in 1974 and deals with carbanion nucleophiles derived from phenylalkanenitriles. The catalyst is triethylbenzylammonium chloride (TEBA).39 ... 

BTF is a suitable solvent for conducting heterogeneous reactions with phase transfer catalysis. The reaction of benzyl chloride with sodium cyanide (in toluene and BTF) or potassium cyanide (in acetonitrile and BTF) using two different phase transfer catalysts [70] gave similar yields (12.1 12.2). Aromatic nucleophilic substitution of chloro-2,4-dinitro benzene using potassium fluoride and... 

Nucleophilic Substitutions. 7V,7V-Dimethyldithiocarbamoyl-acetonitrile (1) serves as an active methylene compound, because its carbanion is stabilized by sulfur and cyano groups. It can be alkylated stepwise in aqueous sodium hydroxide under phase transfer catalysis (eq 1). The anion undergoes nucleophilic aromatic substitution to give nitroarenes, with elimination of the dithiocarbamate group (eq 2). Nucleophilic addition of (1) to phenyl isothiocyanate also occurs readily. ... 

Solid-liquid phase transfer catalyst 2 for aliphatic and aromatic nucleophilic substitution synergistic effect with Cu in Ullmann synthesis as ligand in homogeneous hydrogenation catalysis (see 1st edition). 

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