Journal of the Chemical Society. Perkin transactions II p. 1675 - 1679 (1990)
Update date:2022-08-11
Topics:
Bullen, John V.
Ridd, John H.
o-Nitrophenols with an additional substituent (Y = NO2, Cl, or Me) in the 3-position rearrange in trifluoromethanesulphonic acid at 100 deg C to give mainly the product with the nitro group in the opposite ortho position; no more than 1-4percent of other products are formed.The reactions give first-order kinetics, are acid-catalysed and (at least when Y = NO2) are intramolecular.The rate of rearrangement varies with the 3-substituent in the order Me > Cl > NO2.The results are discussed in terms of a rate-determining migration of the nitro group in the Wheland intermediate formed by protonation at the 2-position.A much slower rearrangement occurs with 3,4-dinitrophenol under the same conditions to give a small yield of 2,5-dinitrophenol accompanied by decomposition of the substrate.
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