✍ Scribed by Mieczysław Mąkosza; Andrzej Kwast
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Hydrogens located at activated positions in electrophilic arenes, e.g. ortho and para hydrogens in nitrobenzenes, can be replaced with a nucleophile moiety provided there is at least one nucleofuge X connected to the nucleophilic centre. As the group really leaving in this hydrogen substitution process is not the hydride anion but X, the reaction has been named vicarious nucleophilic substitution of hydrogen (VNS). The concepts on the mechanism of the reaction and their experimental background are presented. Reactivity and orientation-the fundamental questions concerning synthetical applications of VNS-are discussed in light of the supposed mechanistic picture.
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Hydroxylation of azulenes with tert-butylhydroperoxide active nucleophile, also reacts with unsubstituted azulene. A variety of transformations of 6-hydroxyazulenes, such as proceeds efficiently at the 6-position when the former contain electron-withdrawing substituents in the five-substitution of t