69709-36-0Relevant academic research and scientific papers
Reactions of Organic Anions, 163. - Reactions of Nitrobenzophenones with Carbanions Containing Leaving Groups. Vicarious Nucleophilic Substitution of Hydrogen versus Darzens or Wittig-Horner Reactions
Makosza, Mieczyslaw,Baran, Janusz,Dziewonska-Baran, Danuta,Golinski, Jerzy
, p. 825 - 832 (2007/10/02)
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 i
Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes with Carbanions of α-Haloalkyl Phenyl Sulfones
Makosza, Mieczyslaw,Golinski, Jerzy,Baran, Janusz
, p. 1488 - 1494 (2007/10/02)
Carbanions of α-chloroalkyl phenyl sulfones and N,N-dialkyl-α-chloroalkanesulfonamides react with nitrobenzenes to effect direct nucleophilic replacement of hydrogen ortho and para to the nitro group, with vicarious loss of chloride anion, to give the corresponding nitrobenzylsulfonyl derivatives.The reaction occurs much more rapidly than the replacement of such good leaving groups as halogen, methoxy, and phenoxy.Most substituents in the nitrobenzene ring do not interfere with the reaction.The effect of substituents in the nitrobenzene and the carbanion on the orientation of the substitution is discussed.
REACTIONS OF CHLOROMETHYL PHENYL SULFONE CARBANION WITH NITROBENZOPHENONES. THE VICARIOUS SUBSTITUTION OF HYDROGEN VERSUS THE DARZENS CONDENSATION
Makosza, Mieczyslaw,Golinski, Jerzy,Baran, Janusz,Dziewonska-Baran, Danuta
, p. 1619 - 1622 (2007/10/02)
Carbanion of chloromethyl phenyl sulfone replaces hydrogen atoms o'- and p'- to the nitro group in o-nitrobenzophenone, whereas with p-nitrobenzophenone it enters the Darzens condensation followed by rearrangement and decarbonylation.Reaction course with
