85448-31-3Relevant academic research and scientific papers
Development and Application of a Recyclable High-Load Magnetic Co/C Hybrid ROMP-Derived Benzenesulfonyl Chloride Reagent and Utility of Corresponding Analogues
Faisal, Saqib,Zang, Qin,Maity, Pradip K.,Brandhofer, Agnes,Kearney, Patrick C.,Reiser, Oliver,Grass, Robert N.,Stoianova, Diana,Hanson, Paul R.
, p. 2274 - 2277 (2017)
The development and application of high-load, recyclable magnetic Co/C hybrid ROMP-derived benzenesulfonyl chloride and analogues is reported. The regeneration and utility of these reagents in the methylation/alkylation of various carboxylic acids is demonstrated via efficient retrieval of the magnetic reagent with a neodymium magnet. Additional reactions employing the analogue sulfonic acid and in situ generated magnetic benzenesulfonyl azide are also reported.
TEMPO-Me: An Electrochemically Activated Methylating Agent
Norcott, Philip L.,Hammill, Chelsey L.,Noble, Benjamin B.,Robertson, Johnathon C.,Olding, Angus,Bissember, Alex C.,Coote, Michelle L.
supporting information, p. 15450 - 15455 (2019/11/02)
Bench- and air-stable 1-methoxy-2,2,6,6-tetramethylpiperidine (TEMPO-Me) is relatively unreactive at ambient temperature in the absence of an electrochemical stimulus. In this report, we demonstrate that the one-electron electrochemical oxidation of TEMPO-Me produces a powerful electrophilic methylating agent in situ. Our computational and experimental studies are consistent with methylation proceeding via a SN2 mechanism, with a strength comparable to the trimethyloxonium cation. A protocol is developed for the electrochemical methylation of aromatic acids using TEMPO-Me.
Supramolecular catalysis of esterification by hemicucurbiturils under mild conditions
Cong, Hang,Yamato, Takehiko,Feng, Xing,Tao, Zhu
, p. 181 - 185 (2013/01/14)
Hemicucurbit[6]uril (HemiQ[6])-induced esterification of acids with CH 3OH was investigated. Esterification of the model substrate MA in the presence of different amounts of HemiQ[6] had reaction rate constants of k 0.5 = 0.18 h-1, k1.0 = 0.36 h-1 and k2.0 = 0.52 h-1. These results confirm that the reaction rate increases with the ratio of catalyst to substrate. Ineffective catalysis of MA esterification with a stoichiometric amount of MeOH suggests that the mechanism for HemiQ[6]-catalyzed esterification is solvolysis. Comparing the HemiQ[6]-catalytic kinetics of MA (4-methoxy-4-oxobut-2-enoic acid) with AA (acrylic acid) and BA (benzoic acid) shows that the catalytic activities should bear relation to the size of substrates. The different conversion of sorts of substrates in the presence of HemiQ[6] reveals that the supramolecular catalysis is favor in the conjugated structures. The inefficacy of HemiQ[12] demonstrates that the catalytic capability depends on the structure of the macrocyclic compound used.
