6317-27-7Relevant articles and documents
Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates
Lei, Xiangyang,Jalla, Anusha,Abou Shama, Mhd A.,Stafford, Jamie M.,Cao, Billy
supporting information, p. 2578 - 2585 (2015/09/01)
Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding
Scope of direct arylation of fluorinated aromatics with aryl sulfonates
Chang, Joyce Wei Wei,Chia, Eugene Yurong,Chai, Christina Li Lin,Seayad, Jayasree
supporting information; experimental part, p. 2289 - 2299 (2012/04/10)
The scope and limitations of direct arylation of fluorinated aromatics with aryl sulfonates was examined. Pd(OAc)2, in the presence of MePhos and KOAc in THF, efficiently catalyzed the direct arylation of fluoro aromatics with aryl triflates un
Pitfalls in assessing the α-effect: Reactions of substituted phenyl methanesulfonates with HOO-, OH-, and substituted phenoxides in H2O
Um, Ik-Hwan,Im, Li-Ra,Buncel, Erwin
body text, p. 8571 - 8577 (2011/03/20)
Toward resolving the current controversy regarding the validity of the α-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-1l with HOO-, OH-, and Z-substituted phenoxides in the gas phase versus solu
A novel synthesis of aryl mesylates via one-pot demethylation-mesylation of aryl methyl ethers using a mixture of phosphorus pentoxide in methanesulfonic acid
Kaboudin, Babak,Abedi, Yaghoub
experimental part, p. 2025 - 2028 (2009/12/26)
A simple, efficient, and new method has been developed for the synthesis of aryl mesylates via one-pot demethylation-mesylation of aryl methyl ethers. Treatment of a variety of aryl methyl ethers with a mixture of phosphorus pentoxide in methanesulfonic a
A simple preparation of aryl methanesulfonates by thermal decomposition of dry arenediazonium O-benzenedisulfonimides in methanesulfonic acid
Barbero, Margherita,Degani, Iacopo,Dughera, Stefano,Fochi, Rita,Perracino, Paolo
, p. 90 - 93 (2007/10/03)
Aryl methansulfonates 3 (18 examples) were easily prepared by thermal decomposition of dry arenediazonium o-benzenedisulfonimides 1 in methanesulfonic acid (2). The reactions were carried out at temperatures between 60 and 120°C for times between 0.5 and 8 h. The aryl methanesulfonates were obtained in reproducible yield of 70-90%, with few exceptions. In all cases the o-benzenedisulfonimide (4) could be recovered in good yields which can then be reused to prepare the salts 1. When thermal decomposition of salts 1 was carried out in trifluoromethanesulfonic acid (5) at 90-120°C for 1-2 h, aryl trifluoromethanesulfonates 6 were obtained in 73-78% yield (3 examples).
Sulfonyl esters 7. The second and third sequences in the Trithioorthoformate Reaction
Ginige, Kashyapa Ananda,Goehl, John Edward,Langler, Richard Francis
, p. 1638 - 1648 (2007/10/03)
A previous report has established the intermediacy of a sulfide-sulfonate ester in the one-pot conversion of an aryl mercaptan and a sulfonate ester into the corresponding trithioorthoformate. This report describes evidence for the sequential intermediacy of a bissulfide-sulfonate ester and a dithiosulfene in the conversion of the sulfide-sulfonate ester into the trithioorthoformate. A new sulfonate ester is shown to give the highest yield of trithioorthoformate.
ALKANESULFONYLATION. XIV. MECHANISM OF CATALYSIS OF MESYLATION BY 4-DIMETHYLAMINOPYRIDINE
Bezrodnyi, V. P.,Skrypnik, Yu. G.,Lyashchuk, S. N.,Byalykh, E. V.
, p. 1563 - 1565 (2007/10/02)
Kinetic evidence was obtained for the occurrence of the mesylation of p-chlorophenol in the presence of 4-dimethylaminopyridine by the sulfene path.The product from cycloaddition of methylenesulfene, generated from methanesulfonyl chloride and 4-dimethyla
MECHANISM OF THE REACTION OF (ARYLOXY)TRIMETHYLSTANNANE WITH METHANESULFONYL CHLORIDE - SOLVENT AND SUBSTITUENT EFFECTS ON THE RATE OF THE REACTION.
Kozuka,Yamaguchi,Tagaki
, p. 573 - 576 (2007/10/02)
A kinetic study has been conducted on the reactions of (aryloxy)trimethylstannanes with methanesulfonyl chloride giving chlorotrimethylstannane and aryl methanesulfonates. The reaction was found to obey a second order kinetic equation. The solvent effect on the rate of the reaction appeared obscure although a small rate enhancement was observed in a polar solvent. Substituent effect of the aryloxyl group was found to be dependent on the solvent used while a clear isokinetic relationship was observed. A charge separated four-center transition state has been suggested for the reaction.
ALKANESULFONYLATION REACTIONS IX. CATALYTIC EFFECT OF PYRIDINES ON THE MESYLATION OF PHENOLS
Skrypnik, Yu. G.,Bezrodnyi, V. P.
, p. 2056 - 2063 (2007/10/02)
The kinetics of the mesylation of seven substituted phenols in the presence of 13 derivatives of pyridine in benzene at 50 deg C were investigated.It was shown that in this case, in contrast to catalysis by trialkylamines, the elimination-addition (sulfen