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Reactions of Organic Anions, 163 Reactions of Nitrobenzophenones with Carbanions Containing Leaving Groups. Vicarious Nucleophilic Substitution of Hydrogen versus Darzens or Wittig‐Horner Reactions
Author(s) -
Ma̧kosza Mieczysłw,
Baran Janusz,
DziewońskaBaran Danuta,
Goliński Jerzy
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890233
Subject(s) - carbanion , chemistry , benzophenone , wittig reaction , nucleophilic substitution , medicinal chemistry , nitro , substitution reaction , nucleophile , photochemistry , organic chemistry , catalysis , alkyl
Carbanions containing leaving groups at the carbanion center react with nitrobenzophenones by two general pathways: addition to the carbonyl group which results in the Darzens or Wittig‐Horner reaction and/or addition to the nitroaromatic ring resulting in the vicarious nuclephilic substitution of hydrogen. The former pathway dominates for p ‐nitrobenzophenone, and the vicarious nuclephilic substitution is the major process for o ‐nitro‐benzophenone; the extent of these two reactions for m ‐nitrobenzophenone depends on the type of carbanion and the reaction conditions.