The reactivity of organophosphorus compounds. Part XXV. Displacement of activated aromatic nitro-groups by tervalent phosphorus reagents
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 10,p. 1314-1318
- https://doi.org/10.1039/j39690001314
Abstract
A novel displacement of certain activated aromatic nitro-groups by tervalent organophosphorus reagents is described. Thus trimethyl, triethyl, and tri-isopropyl phosphites, diethyl methylphosphonite, and ethyl diphenyl-phosphinite react with increasing ease [(RO)3P < (EtO)2PMe < EtOPPh2] with o-dinitrobenzene to give high yields of the corresponding dialkyl o-nitrophenylphosphonates, ethyl P-methyl-o-nitrophenylphosphinate, and o-nitrophenyldiphenylphosphine oxide, respectively, and ethyl nitrite. 1,2,4-Trinitrobenzene undergoes similar displacements to give 2,4-dinitrophenyl derivatives. Under comparable conditions p-dinitrobenzene and o-chloronitrobenzene do not undergo these reactions other than, possibly, to a very minor extent.Keywords
This publication has 0 references indexed in Scilit: