Tetrahedron p. 1901 - 1912 (1998)
Update date:2022-08-03
Topics: Elemental analysis Asymmetric synthesis Regioselectivity Diastereoselectivity Green chemistry Solid-phase synthesis Microwave-assisted synthesis Distillation Catalyst Thin-layer chromatography (TLC) Ligand Molecular docking Stereochemistry Lead compound Enantioselectivity Steric hindrance Enantiomeric excess (ee) Recrystallization Mass spectrometry (MS) Nucleophilic substitution Differential scanning calorimetry (DSC) Atom economy Pharmacophore Kinetics High-performance liquid chromatography (HPLC) Infrared spectroscopy (IR) Electrochemistry Deprotection Filtration Solvent polarity Protecting group Nuclear Magnetic Resonance (NMR) Resolution X-ray crystallography Leaving group Density functional theory (DFT) Enzyme inhibition High-Throughput Screening Scale-up Steric Effects Chemoselectivity Nucleophilic Attack Reaction Mechanism Electronic effects UV-Vis Spectroscopy Cyclic Voltammetry (CV) Toxicity Assessment Virtual Screening Substrate Scope Controlled Release
Braverman, Samuel
Zafrani, Yossi
A new and convenient method for the preparation of trichloro and trifluoromethanesulfinates is described. These esters readily undergo rearrangement to the corresponding sulfones at room temperature, in high yields. In contrast to trichloromethyl sulfoxides which undergo base-induced β-elimination of chloroform to sulfines, the corresponding sulfones undergo an unusually facile Ramberg-Backlund rearrangement with formation of dichloromethylene products. Replacement of CCl3 by CF3 results in complete loss of reactivity, even under drastic basic conditions.
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Doi:10.1021/acs.orglett.5b00009
(2015)Doi:10.1039/a705673g
(1998)Doi:10.1039/c3dt32992e
(2013)Doi:10.1002/anie.200500683
(2006)Doi:10.1039/b601160h
(2006)Doi:10.1021/ja01313a039
(1935)
