70951-74-5Relevant academic research and scientific papers
A three-component coupling process based on vicarious nucleophilic substitution (VNSAR)-alkylation reactions: An approach to indoprofen and derivatives
Lawrence, Nicholas J.,Liddle, John,Bushell, Simon M.,Jackson, David A.
, p. 457 - 464 (2007/10/03)
The intermediate anion derived from the vicarious nucleophilic substitution (VNS) of hydrogen reacts with a series of alkyl halides to generate the corresponding α-alkylated conventional VNS product in a one-pot process. This one-pot VNS-alkylation reaction offers a convenient route to a range α-substituted nitrobenzyl phosphine oxides, sulfones, and esters via a three-component coupling reaction. Reactions of α-chloroethyl phenyl sulfone (14) and ethyl 2-chloropropionate (16) with nitrobenzene followed by subsequent addition of an alkylating agent give a series of sulfones and esters bearing an α-aryl quaternary center. The VNS-alkylation protocol has been applied to the synthesis of derivatives of Indoprofen from nitrobenzene using readily available inexpensive starting materials. Indoprofen itself was prepared using the conventional VNS reaction in four steps and 24% overall yield from nitrobenzene.
Electron-transfer substitution reactions: The p-nitrocumyl system
Kornblum, Nathan,Cheng, Leung,Davies, Thomas M.,Earl, Gary W.,Holy, Norman L.,Kerber, Robert C.,Kestner, Melvin M.,Manthey, Joseph W.,Musser, Michael T.,Pinnick, Harold W.,Snow, Donald H.,Stuchal, Francis W.,Swiger, Roger T.
, p. 196 - 204 (2007/10/02)
Facile substitution reactions at the tertiary carbon of p-nitrocumyl chloride and α,p-dinitrocumene are described. These reactions occur with a wide range of organic and inorganic nucleophiles and are noteworthy for providing novel and powerful means of synthesis; they occur readily under mild conditions, give excellent yields of pure products, and, in contrast to SN2 displacements, are rather insensitive to steric hindrance. They are, therefore, especially valuable for the preparation of highly branched compounds. The view that these are electron-transfer chain processes derives from inhibition studies and, also, from the fact that these reactions are induced by one-electron-transfer agents.
Electron-Transfer Chain-Substitution Reactions of Ambident Anions
Kornblum, Nathan,Ackermann, Peter,Swiger, R. T.
, p. 5294 - 5298 (2007/10/02)
A simple explanation is proposed for the fact that electron-transfer chain-substitution reactions involving ambident anions give only one of the two possible products and experimental evidence which supports this hypothesis is presented.
