77334-52-2Relevant academic research and scientific papers
An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent
Pinna, Giovanni,Bellucci, Maria Cristina,Malpezzi, Luciana,Pisani, Laura,Superchi, Stefano,Volonterio, Alessandro,Zanda, Matteo
, p. 5268 - 5281 (2011/08/06)
N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for α-hydroxy, α-chloro, and α-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective α-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.
A Systematic Study of Benzyl Cation Initiated Cyclization Reactions
Angle, Steven R.,Louie, Michael S.
, p. 2853 - 2866 (2007/10/02)
A systematic investigation of benzyl cation inititiated cyclization reactions to form six-membered carbocycles is presented.The generation of benzyl cations from benzylic bromides, ethers, and alcohols followed by intramolecular capture provided good yields of cyclized products by use of several different cyclization terminators (e.g., phenyl, alkene, β-keto ester).A study on the effect of changing the electronic nature of substituents para to the benzyl cation showed that even electron-withdrawing substituents such as quaternary ammonium afford high yields of cyclization products.The formation of five- and seven-membered carbocycles was briefly investigated and found to be less general than the formation of the corresponding six-membered carbocycles.
