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p ‐Quinoid Compounds by Nucleophilic Aromatic Substitution with Hydride as Leaving Group
Author(s) -
Hagel Marcel,
Liu Jianhui,
Muth Oliver,
Estevez Rivera Hebert Jesus,
Schwake Erik,
Sripanom Lertnarong,
Henkel Gerald,
Dyker Gerald
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700177
Subject(s) - chemistry , hydride , nucleophile , nucleophilic aromatic substitution , nucleophilic substitution , leaving group , steric effects , substitution reaction , medicinal chemistry , cationic polymerization , tributyltin hydride , group (periodic table) , stereochemistry , organic chemistry , catalysis , hydrogen
Triarylmethylium tetrafluoroborates with a sterically shielded cationic center react with selected C‐ and N‐nucleophiles under nucleophilic aromatic substitution to give dipolar p ‐quinoid final products. The mechanistic rationale includes a hydride leaving group in analogy to the Tschitschibabin reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)