71838-14-7Relevant academic research and scientific papers
THE EFFECT OF ORTHO SUBSTITUENTS IN SRN1 REACTIONS. SOME SYNTHETIC APPLICATIONS.
Bunnett, Joseph F.,Mitchel, Eric,Galli, Carlo
, p. 4119 - 4132 (1985)
Several ortho-substituted iodobenzenes were allowed to react, via the SRNl mechanism, with mixtures of diethyl phosphite ion and pinacolone enolate ion.From product composition data, the relative reactivities of the two nucleophiles were reckoned.They represent relative reactivities in attachment to aryl radical intermediates.Most of the ortho effects are slight, but there is evidence that large ortho substituents hinder attachment of the phosphite more than the enolate nucleophile.The methoxy and diethoxyphosphoryl substituents, when para to the site of substitution, respectively favour and disfavour the phosphite with respect to the enolate ion.SRNl reactions of ortho-substituted halobenzenes are, for some substituents, followed by other reactions which afford products of synthetic interest.
Direct synthesis of ortho-halogenated arylphosphonates via a three-component reaction involving arynes
Chen, Qian,Han, Yukun,Hu, Yifan,Huang, Yuanting,Huo, Yanping,Li, Xianwei,Ou, Yingcong
, p. 7010 - 7018 (2021/05/29)
A three-component reaction involving arynes, trialkyl phosphites, and halides has been achieved under mild reaction conditions. This transformation provides a direct synthetic approach to ortho-halogenated arylphosphonates, which could be rapidly converted to diversely ortho-functionalized arylphosphorus com ounds
Aromatic nucleophilic polysubstitution by sequential SRN1 reactions
Beugelmans, Rene,Chbani, Mohamed
, p. 290 - 305 (2007/10/02)
Substitution of aromatics (benzene, naphthalene and pyridine) by two or three distinct nucleophiles derived from phosphonates and/or thiolates can be performed by sequential photosimulated SRN1 reactions whose radical chain mechanism is compatible with the successively introduced substituents. aromatic polysubstitution / SRN1 mechanism / disubstituted aromatic / trisubstituted aromatic / distinct substituent
