Nucleophilic Neutralization of Organophosphates: Lack of Selectivity or Plenty of Versatility?

Silva V.B.; Campos R.B.; Pavez P.; Medeiros M.; Orth E.S.

Keywords: dephosphorylation, organophosphorus compounds, phosphate esters, nucleophilic catalysis, organothiophosphates

Abstract

Neutralization of organophosphates is an issue of public health and safety, involving agrochemicals and chemical warfare. A promising approach is the nucleophilic neutralization, scope of this review, which focuses on the molecular nucleophiles: hydroxide, imidazole derivatives, alpha nucleophiles, amines and other nucleophiles. A reactivity mapping is given correlating the pathways and reaction efficiency with structural dependence of the nucleophile (basicity) and the organophosphate (electrophilic centers, P=O/P=S shift, leaving and non-leaving group). Reactions extremely unfavorable (>20 years) can be reduced to seconds with various nucleophiles, some which are catalytic. Although there is no universal nucleophile, a lack of selectivity in some cases accounts for plenty of versatility in other reactions. The ideal neutralization requires a solid mechanistic understanding, together with balancing factors such as milder conditions, fast process, selectivity and less toxic products.

Más información

Título según WOS: Nucleophilic Neutralization of Organophosphates: Lack of Selectivity or Plenty of Versatility?
Título según SCOPUS: Nucleophilic Neutralization of Organophosphates: Lack of Selectivity or Plenty of Versatility?
Título de la Revista: Chemical Record
Volumen: 21
Número: 10
Editorial: John Wiley and Sons Inc.
Fecha de publicación: 2021
Página final: 2665
Idioma: English
DOI:

10.1002/tcr.202100123

Notas: ISI, SCOPUS