Tetrahedron p. 5205 - 5208 (1988)
Update date:2022-08-11
Topics:
Galli, Carlo
While nitroarylhalides are unreactive in SRN1 reactions, o-iodonitrobenzene (1) gives an efficient nucleophilic substitution with pinacolone enolate ion under photostimulation in liquid ammonia.The observed reactivity of (1) confirms the high rate of fragmentation of the C-I bond of this substrate, as determined in the literature by electrochemical measurements.The origin of such reactivity is traced to the steric inhibition of conjugation of the nitro group with the aromatic ring, as due to the presence of the bulky iodine atom in the ortho position.
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