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Vicarious nucleophilic substitution of hydrogen. Mechanism and orientation
Author(s) -
Mąkosza Mieczysław,
Kwast Andrzej
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199805)11:5<341::aid-poc22>3.0.co;2-t
Subject(s) - chemistry , nucleophile , moiety , hydride , nucleophilic substitution , reactivity (psychology) , electrophile , substitution reaction , stereochemistry , hydrogen , leaving group , mechanism (biology) , medicinal chemistry , catalysis , organic chemistry , medicine , alternative medicine , pathology , philosophy , epistemology
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.