New Synthesis of Optically ActiveO-ArylO-Ethyl Phenylphosphonothionates | Zendy

Hiromichi Yoshikawa | Zendy

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New Synthesis of Optically ActiveO-ArylO-Ethyl Phenylphosphonothionates

Author(s) -

Hiromichi Yoshikawa

Publication year - 1999

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.63.424

Subject(s) - aryl , yield (engineering) , chemistry , ethyl ester , racemization , phosphoric acid , organic chemistry , sodium , medicinal chemistry , alkyl , materials science , metallurgy

The mixed anhydride method was applied to synthesize O-aryl O-ethyl phenylphosphonothionate. The reaction of O, O-diethyl phosphorochloridate with O-ethyl phenylphosphonothioic acid afforded O, O-diethyl phosphoric O-ethyl phenylphosphonothioic anhydride in a good yield. This anhydride was converted to O-aryl O-ethyl phenylphosphonothionates by reacting with the appropriate sodium phenoxide. This esterification occurred without racemization and produced optically pure O-ethyl O-(4-nitrophenyl) phenylphosphonothionate (EPN) and O-(4-cyanophenyl) O-ethyl phenylphosphonothionate (cyanofenphos).

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