3771-17-3Relevant academic research and scientific papers
Friedel–Crafts Alkylation with Carbenium Ions Generated by Electrochemical Oxidation of Stannylmethyl Ethers
Jirgensons, Aigars,Lielpetere, Anna
, (2020/07/27)
The electrochemical activation of stannylmethyl ethers was exploited for Friedel–Crafts alkylation of arenes at near-neutral conditions. Single cell anodic oxidation of stannylmethyl ethers leads to oxonium ions which fragment to carbenium ions in the pre
Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes
Bering, Luis,Jeyakumar, Kirujan,Antonchick, Andrey P.
supporting information, p. 3911 - 3914 (2018/07/22)
A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.
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.
Hydroxy substituted phenyltetralines: compounds with affinity for estrogen and androgen receptors
Schneider,Schiller
, p. 17 - 21 (2007/10/02)
Among nonsteroidal antiandrogens, mostly compounds of the Flutamide-type are described. For the development of new compounds with affinity to androgen receptors and antiandrogenic activity five new hydroxy-substituted phenyltetralines were prepared and te
CATIONIC CYCLIZATION REACTIONS INITIATED BY STABILIZED BENZYL CATIONS
Angle, Steven R.,Louie, Michael S.
, p. 5741 - 5744 (2007/10/02)
The in situ generation of stabilized benzyl cations and their subsequent use in cyclization reactions with a monosubstituted benzene, a furan and a β-keto ester terminators is described.
