Regioselectivity in S<sub>N</sub>H reactions of some 3‐nitro‐1,8‐naphthyridines with chloromethyl phenyl sulfone

Grzegożek, Maria; Woźniak, M.; Barański, A.; Plas, H. C. Van Der

doi:10.1002/jhet.5570280440

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Vicarious nucleophilic substitution of hydrogen. Mechanism and orientation

Mąkosza

Kwast

1998

J. Phys. Org. Chem.

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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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