49806-13-5Relevant academic research and scientific papers
Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride
Laudadio, Gabriele,Bartolomeu, Aloisio De A.,Verwijlen, Lucas M. H. M.,Cao, Yiran,De Oliveira, Kleber T.,No?l, Timothy
supporting information, p. 11832 - 11836 (2019/08/26)
Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.
ALKANESULFONYLATION.XX. CATALYSIS OF THE PHENOLYSIS OF ALKANESULFONYL CHLORIDES IN PROTON-INERT MEDIA CATALYZED BY PYRIDINE BASES. THE EFFECT OF THE SUBSTRATE STRUCTURE
Skrypnik, Yu. G.,Lyashchuk, S. N.
, p. 695 - 700 (2007/10/02)
The kinetics of the reaction of methane-, ethane-, propane-, 1-methylmethane-, and cyclohexanesulfonyl chlorides and also of substituted phenylmethanesulfonyl chlorides with phenol in the presence of pyridine in chlorobenzene at 303 K were studied by GLC
ALKANESULFONYLATION. XIII. SOLVATION EFFECTS OF THE SOLVENT ON THE COMPETING MECHANISMS OF ALKANESULFONYLATION OF PHENOL UNDER CONDITIONS OF CATALYSIS BY TERTIARY AMINES
Bezrodnyi, V. P.,Lyashchuk, S. N.,Skrypnik, Yu. G.
, p. 1128 - 1132 (2007/10/02)
Change in the nature of the solvent leads to a significant change in the ratio of the competing mechanisms in alkanesulfonylation, i.e., the sulfene (1a) and general base catalysis (1b).The most important role here is played by the polarity of the medium, and with increase in the polarity the predominant path changes from (1b) to (1a).In the case of mechanism (1b) the effects of specific solvation show up more strongly than for mechanism (1a).This is due to differences in the structure of the transition states.A quantitative assessment of the solvation effects on the competing paths (1a,b) is given.
ALKANESULFONYLATION REACTIONS. XII. EFFECT OF THE NATURE OF THE SOLVENT ON THE RATE AND MECHANISM OF THE PROPANESULFONYLATION OF PHENOL IN THE PRESENCE OF DIMETHYLBENZYLAMINE
Bezrodnyi, V. P.,Lyashchuk, S. N.,Skrypnik, Yu. G.
, p. 737 - 741 (2007/10/02)
The kinetics of the reaction of propanesulfonyl chloride with phenol in the presence of dimethylbenzylamine in p- and m-xylene, toluene, chloroform, chlorobenzene, methylene chloride, and nitrobenzene at 30 deg C were studied by GLC and potentiometric titration.The degree of reaction by the sulfene mechanism increases with increase in the polarity of the medium, and the contribution from the mechanism of general base catalysis decreases.The effect of the solvent polarity on the reaction rate is described by the Kirkwood equation.Structures are proposed for the transition states of the concurrent reaction mechanisms.
ALKANESULFONYLATION REACTIONS. X. EFFECT OF THE STRUCTURE OF THE ALKANESULFONYL HALIDE ON THE FORMATION OF PHENYLALKANESULFONATES CATALYZED BY TRIETHYLAMINE
Bezrodnyi, V. P.,Skrypnik, Yu. G.
, p. 1660 - 1665 (2007/10/02)
The kinetics of the reactions of methane-, propane-, isopropane-, cyclohexane, and phenylmethanesulfonyl chlorides and propanesulfonyl bromide with phenol in the presence of triethylamine in benzene at 30 deg C were investigated by GLC and potentiometric
ALKANESULFONYLATION REACTIONS. XI. THE EFFECT OF THE STRUCTURE OF PHENOLS ON THE REACTION WITH PROPANESULFONYL CHLORIDE IN THE PRESENCE OF TRIBUTYLAMINE
Bezrodnyi, V. P.,Skrypnik, Yu. G.
, p. 2349 - 2352 (2007/10/02)
The kinetics of the reaction of eight substituted phenols XC6H4OH with propanesulfonyl chloride in the presence of tributylamine in benzene at 30 deg C were studied by potentiometric titration.The effect of the structure of the phenols is described by a two-parameter Hammett equation, which takes separate account of the induction and mesomeric effects of X and favors a mechanism of general base catalysis.
