Journal of the Chemical Society. Perkin transactions II p. 189 - 192 (1987)
Update date:2022-08-17
Topics:
Bowden, Keith
Nadvi, Nighat S.
The rate coefficients for the methoxide-catalised methanolysis of a series of 1-substituted 2,4-dinitrobenzenes and 2-substituted 5-nitropyridines have been measured in methanolic DMSO at 20.0 or 21.0 deg C.For the 2-substituted 5-nitropyridines and for the 1-substituted 2,4-dinitrobenzenes below ca. 55 mol percent DMSO, the rates have been correlated with an acidity function of the medium.The slopes of these linear relations are discussed.The 1-substituted 2,4-dinitrobenzenes above ca. 55 mol percent DMSO give rise to Meisenheimer complexes as intermediates and/or as the product of the reaction.The product of the reaction then becomes the 1,1-Meiseheimer complex of methoxide and 2,4-dinitroanisole.For the 1-fluoro substrate the formation of the latter becomes rate determining.For other 1-substituted substrates the decomposition of a 1,3-Meisenheimer complex becomes rate determining.
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