1199-67-3Relevant articles and documents
Comparative Study of the Water-Catalyzed Hydrolysis of methyl Perchlorate in 1,4-Dioxane-Water and in 1,3-Dioxane-Water
Remerie, Klaas,Engberts, Jan B. F. N.
, p. 3543 - 3546 (1981)
Pseudo-first-order rate constants (kobsd) and thermodynamic activation parameters have been compared for the water-catalyzed hydrolysis of H2O = 0.80 and most likely reflect the specific hydrogen bonding interactions between water and the organic cosolvent.The structural properties of both aqueous binaries are critically discussed, and it is concluded that the maxima inkobsd at about nH2O = 0.80 in both solvent mixtures do not reflect an enhanced degree of water structure at this solvent composition.
Visible-Light Photoredox Catalyzed Oxidative/Reductive Cyclization Reaction of N-Cyanamide Alkenes for the Synthesis of Sulfonated Quinazolinones
Qian, Ping,Deng, Yu,Mei, Haibo,Han, Jianlin,Zhou, Jie,Pan, Yi
, p. 4798 - 4801 (2017)
An efficient photocatalytic oxidative/reductive cyclization reaction of N-cyanamide alkenes with arylsulfinic acids or arylsulfonyl chlorides, which proceeds through C-S, C-C, and C-N bond formations, is reported. This photocatalytic reaction was carried out under mild conditions, which provides a new strategy for the synthesis of sulfonated quinazolinones. Furthermore, a one-pot procedure to achieve terminal alkenes has been explored via elimination of the obtained sulfonated quinazolinones under basic conditions.
tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines
Kuang, Kaimo,Wu, Meixia,Wu, Sixin,Xia, Ziqin,Xu, Qiankun,Zhang, Man,Zhou, Nengneng
supporting information, p. 3491 - 3495 (2021/06/28)
A tert-butyl hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfinic acids for the construction of sulfonated benzoxepines is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodology features mild reaction conditions, a broad substrate scope and good functional group tolerance. (Figure presented.).
Direct Irradiaton of Aryl Sulfides: Homolytic Fragmentation and Sensitized S-Oxidation
Bonesi, Sergio M.,Crespi, Stefano,Merli, Daniele,Manet, Ilse,Albini, Angelo
, p. 9054 - 9065 (2017/09/11)
The direct irradiation of diphenyl sulfide and p-substituted thioanisoles in the presence of oxygen was investigated by means of both steady state and laser flash photolysis experiments. Two competitive pathways took place from the triplet excited state o
A General, One-Pot Method for the Synthesis of Sulfinic Acids from Methyl Sulfones
Gauthier, Donald R.,Yoshikawa, Naoki
supporting information, p. 5994 - 5997 (2016/12/09)
A simple and efficient method for converting methyl sulfones to sulfinic acids is described. The process involves alkylation with a benzylic halide, followed by in situ elimination of the resulting styrene in the presence of excess base to yield a sulfinic acid in a single reaction process. The usefulness of the alkylation-elimination sequence is demonstrated by generating a variety of sulfinic acids from methyl sulfones. Late stage functionalization and 14C-labeling of several biologically active methyl sulfones were accessed via sulfinate intermediates.
Copper-mediated cascade synthesis of diaryl sulfones via the sandmeyer reaction
Yang, Xiaobo,Shi, Liangliang,Fu, Hua
supporting information, p. 847 - 852 (2014/04/17)
A convenient and efficient method for the copper-mediated cascade synthesis of diaryl sulfones via the Sandmeyer reaction has been developed. The protocol uses readily available aryl amines and arylsulfinic acids as the starting materials, isoamyl nitrite as the diazotizating reagent of the aryl amines, and the method shows mild reaction conditions and high tolerance towards various functional groups in the substrates. Georg Thieme Verlag Stuttgart New York.
Kinetics of the Reaction of 2,4-Dinitrophenyl-4'-substituted Phenyl Sulfones with Morpholine in Methanol
El-Mallah, Nabila M.,Hamed, E. A.,El-Bardan, A. A.
, p. 319 - 328 (2007/10/03)
The rates of morpholine-desulfonylation of 2,4-dinitrophenyl-4'-substituted phenylsulfones (1-6: aryl = 4-Y-C6H4, Y = H, CH3, OCH3, Br, Cl and NO2) have been measured in methanol at different temperatures (25 deg C-40 deg C) and the activation parameters were calculated.A good Hammett correlation was obtained with ρ values of 0.43-0.75.The plot ΔH(excit.) versus ΔS(excit.) gave an isokinetic temperature at 339 deg K.
Nitrosations with hydrazine derivatives: Synthesis of N4-arenesulfinylsemicarbazides and N5-arenesulfinyl-N1-aminobiuretes from arenesulfinylisocyanates and N,N-disubstituted hydrazines
Hanefeld,Landwehr
, p. 344 - 351 (2007/10/02)
Arenesulfinyl-isocyanates 5 prepared in situ from arenesulfinyl chlorides 4 and silver cyanate react with N,N-disubstituted hydrazines to mixtures of N4-arenesulfinylsemicarbazides 6 as main components and N5-arenesulfinyl-N1/s
The acidities of 4-arylsulfonylmethylpyridines and N-methyl and N-benzyl 4-arylsulfonylmethylpyridinium cations in aqueous solution
Wodzinski, Stefan,Bunting, John W.
, p. 2635 - 2644 (2007/10/02)
The pKa values for the deprotonation of a series of 4-(X-phenylsulfonylmethyl)pyridines (6) (pKa = 19.89 (X = H); ρ = 3.0) were determined in aqueous dimethyl sulfoxide solutions at 25 deg C using the H0q acidit
Flow cell electrosynthesis of phenylhydroxylamines. In situ reaction with arenesulfonyl chlorides. A convenient route to arenesulfinic acids synthesis.
Moinet, C.,Raoult, E.
, p. 214 - 221 (2007/10/02)
First, electrosyntheses of phenylhydroxylamines in a flow cell fitted with porous cathode and two counter-electrodes are described.Good yields are attained when electrolyses are performed in buffered aqueous organic or aqueous media.Reaction between p-toluenesulfonyl chloride and N-(3-chloro-4-methylphenyl)hydroxylamine, at the outlet of the cell, leads to a N-sulfonylated phenylhydroxylamine (N-addition); hydrolysis of this latter occurs in aqueous basic media to give the corresponding nitrosobenzene and sodium p-toluenesulfinate.As a result, some arenesulfinic acids have been directly obtained after reaction of arenesulfonyl chloride with sodium salt of 3-hydroxylaminobenzoate and 3-hydroxylaminobenzenesulfonate in aqueous phosphate buffer (pH 7).Next, an examination of the reaction of p-toluenesulfonyl chloride with phenylhydroxylamine in organic solvent, in the presence of triethylamine or of sodium carbonate, shows the importance of experimental conditions to control N-addition or O-addition.Addition of some arenesulfonyl chlorides to phenylhydroxylamine, in ether or dichloromethane containing sodium carbonate, gives only the N-sulfonylated phenylhydroxylamines.These compounds lead to nitrosobenzene and arenesulfinate anions in aqueous basic media.Aliphatic or aromatic sulfinic acids can be prepared in this way.
