Journal of the Chemical Society. Perkin transactions II p. 489 - 492 (1989)
Update date:2022-08-11
Topics:
Cho, Bong Rae
Lee, Jong Chan
Cho, Nam Soon
Kim, Kee Dong
Reactions of the (E)-O-arylbenzaldehyde oximes (1; Ar = 2,4-dinitrophenyl), (2; Ar = p-nitrophenyl), and (3; Ar = phenyl) with OH- in 60 percent aq.DMSO have been investigated.The eliminations are quantitative, producing only benzonitriles and aryloxides.The observation of second-order kinetics, K2OD-/k2OH- = 1.15 - 1.84, and βlg = -0.59 is consistent with an E2 mechanism.The Hammett ρ and k2OD-/k2OH- values increased with poorer leaving groups.For a given substrate the k2OD-/k2OH- value remained (within experimental error) roughly constant, in spite of changes in the β-aryl substituents.These changes in transition state parameters can be interpreted in term of the differing nitrile-forming transition states involved.
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