Synthesis of alpha-(nitroaryl)benzylphosphonates via oxidative nucleophilic substitution of hydrogen in nitroarenes.
Carbanions of diethyl benzylphosphonate and diethyl 1-phenylethylphosphonate add to nitroarenes to form relatively long-lived sigma(H) adducts that can be oxidized to products of oxidative nucleophilic substitution of hydrogen. By variation of the conditions, o- and p-nitroarylated derivatives of the starting phosphonates can be synthesized regioselectively. It has been proven that addition of carbanions of diethyl benzylphosphonate and diethyl 1-phenylethylphosphonate to nitroarenes is a fast process and the respective sigma(H) adducts are formed almost quantitatively.
Makosza
Mieczysław
M
Institute of Organic Chemistry PAS, Kasprzaka 44/52, 00-224 Warszawa, Poland. icho-s@icho.edu.pl
Sulikowski
Daniel
D
D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction
D006841:Hydrocarbons, Aromatic; D063065:Organophosphonates; D016877:Oxidants; D006859:Hydrogen