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- W1998415064 abstract "Upon treatment of o- and p-(phenylseleno)nitrobenzenes with sodium methoxide quantitative exchange reactions took place, affording the corresponding methoxynitrobenzenes. Upon reaction between 2,4-bis(phenylseleno)nitrobenzene 2 and sodium methoxide, an unusual regiopure formation of 4-methoxy-2-(phenylseleno)nitrobenzene 3 was observed. This product remained unreactive toward an excess of sodium methoxide, thus preventing the formation of 2,4-dimethoxynitrobenzene 6. The nature of the reactants and of the intermediate Meisenheimer complexes was examined by synthetic investigations, x-ray crystallography, and DFT calculations. We found that the observed selectivity can be understood in terms of traditional resonance considerations. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:101–108, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20519" @default.
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- W1998415064 date "2009-01-01" @default.
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- W1998415064 title "Sparing the ortho-position in nucleophilic aromatic substitution-specific displacement of the 4-SePh group in 2,4-bis(phenylseleno)nitrobenzene" @default.
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- W1998415064 doi "https://doi.org/10.1002/hc.20519" @default.
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