cas 1950-69-2, 4-Toluenesulfonyl bromide | Articles data

Articles about 1950-69-2Total 24 be found

Article title
Article abstract
Author
Journal number and time
Download

Solid-phase intermolecular radical reactions 1. Sulfonyl radical addition to isolated alkenes and alkynes
The addition of toluenesulfonyl radicals to solid-supported alkenes and alkynes gives bromo-sulfonyl alkenes and alkanes in good yields.
Caddick, Stephen,Hamza, Daniel,Wadman, Sjoerd N.
p. 7285 - 7288
(1999)
Read Online

A Convenient Route to 2-Bromo-3-chloronorbornadiene and 2,3-Dibromonorbornadiene
Substituted norbornadienes are useful in a wide range of applications, including molecular solar-thermal (MOST) energy storage systems. An important precursor for 2,3-substituted norbornadienes is 2-bromo-3-chloronorbornadiene, where the two halogen atoms
Lennartson, Anders,Quant, Maria,Moth-Poulsen, Kasper
p. 1501 - 1504
(2015)
Read Online

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
(2021/09/20)

N,N′-Disulfonylhydrazines: New sulfonylating reagents for highly efficient synthesis of (E)-vinyl sulfones at room temperature
N,N′-Disulfonylhydrazines have been proven to be the most reactive precursors of sulfonyl radicals in all types of sulfonyl substituted hydrazines as early as a half century ago. But such function has not been applied in organic synthesis except the formation of disulfones by self-dimerization of sulfonyl radicals. In this article, they were introduced as new sulfonylating reagents and their combinations with NIS and Et3N were established as excellent iodosulfonylating reagents for alkenes. Finally, a highly efficient method for the synthesis of (E)-vinyl sulfones was developed by mixing an alkene, a N,N′-disulfonylhydrazine, NIS and Et3N in THF at room temperature for 5 min.
Hu, Yuefei,Luo, Dongping,Min, Lin,Shan, Lidong,Wang, Xinyan,Zheng, Weiping
(2020/02/18)

Norbornadiene-bridged diarylethenes and their conversion into turn-off fluorescent photoswitches
We describe the synthesis and characterization of novel diarylethene photoswitches that contain a norbornadiene bridge and operate as p-type positive photochromes. One of the double bonds of norbornadiene is furthermore utilized to attach a fluoresceine tetrazine by an iEDDA cascade reaction, thereby forming a turn-off mode fluorescent photoswitch. This journal is
Büllmann, Simon M.,J?schke, Andres
supporting information
p. 7124 - 7127
(2020/07/14)

Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot
Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.
Equbal, Danish,Singh, Richa,Saima,Lavekar, Aditya G.,Sinha, Arun K.
supporting information
p. 2660 - 2675
(2019/03/14)

Electrochemically induced oxidative S-O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles
The process of oxidative S-O coupling under the action of electric current was developed. Aryl, hetaryl and alkyl sulfonyl hydrazides and N-hydroxy compounds (N-hydroxyimides and N-hydroxybenzotriazoles) are applied as starting reagents for the preparation of sulfonates. The reaction is carried out under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode under a high current density (60 mA cm?2). NH4Br in this process acts as a supporting electrolyte and participates in the oxidation of the starting compounds to form a coupling product. The developed strategy represents a quite atom-efficient approach: one partner loses two nitrogen and three hydrogen atoms, while another one loses only one hydrogen atom. Cyclic voltammetry and the control experiment allowed us to propose possible reaction pathways: generated through anodic oxidation molecular bromine or its higher oxidation state derivatives oxidize the starting compounds to form reactive species, which couple to form the S-O bond.
Terent'ev, Alexander O.,Mulina, Olga M.,Parshin, Vadim D.,Kokorekin, Vladimir A.,Nikishin, Gennady I.
supporting information
p. 3482 - 3488
(2019/04/14)

Copper-Catalyzed Difunctionalization of Allenes with Sulfonyl Iodides Leading to (E)-α-Iodomethyl Vinylsulfones
A highly regioselective iodosulfonylation of allenes in the presence of CuI and 1,10-phenanthroline has been developed for the synthesis of various useful (E)-α-iodomethyl vinylsulfones in moderate to excellent yields. This practical reaction is fast, operationally simple, and in particular, proceeds under very mild conditions to afford the target products with high regio- and stereoselectivity. The selectivity was illustrated by a conceptual DFT analysis.
Lu, Ning,Zhang, Zhiguo,Ma, Nana,Wu, Conghui,Zhang, Guisheng,Liu, Qingfeng,Liu, Tongxin
supporting information
p. 4318 - 4322
(2018/07/29)

PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
p. 2360 - 2364
(2018/05/24)

Cobalt bis(acetylacetonate)–tert-butyl hydroperoxide–triethyl-silane: A general reagent combination for the Markovnikov-selective hydrofunctionalization of alkenes by hydrogen atom transfer
We show that cobalt bis(acetylacetonate) [Co(acac)2], tert-butyl hydroperoxide (TBHP), and triethylsilane (Et3SiH) constitute an inexpensive, general, and practical reagent combination to initiate a broad range of Markovnikov-selective alkene hydrofunctionalization reactions. These transformations are believed to proceed by cobalt-mediated hydrogen atom transfer (HAT) to the alkene substrate, followed by interception of the resulting alkyl radical intermediate with a SOMOphile. In addition, we report the first reductive couplings of unactivated alkenes and aryldiazonium salts by an HAT pathway. The simplicity and generality of the Co(acac)2–TBHP–Et3SiH reagent combination suggests it as a useful starting point to develop HAT reactions in complex settings.
Ma, Xiaoshen,Herzon, Seth B.
supporting information
p. 2259 - 2265
(2018/09/14)

Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions
An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.
Jereb, Marjan,Hribernik, Luka
supporting information
p. 2286 - 2295
(2017/07/24)

METHOD FOR PRODUCING SULFONYL BROMIDE COMPOUNDS
PROBLEM TO BE SOLVED: To provide a method capable of producing sulfonyl bromide compounds which are useful as an intermediate such as a medicine, an agrochemical and a functional materials safely, simply and in a high yield. SOLUTION: There is provided a
-
Paragraph 0028; 0033

(2017/04/27)

Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.
Silva-Cuevas, Carolina,Perez-Arrieta, Carlos,Polindara-García, Luis A.,Lujan-Montelongo, J. Armando
supporting information
p. 2244 - 2247
(2017/05/16)

Synthesis of sulfonamides from azoles and sodium sulfinates at ambient temperature
NBS or NIS mediated direct S[sbnd]N bond formation between azoles and sodium sulfinates is described. The reaction shows good substrate scope and tolerates a wide range of functionalities in both azoles and sodium sulfinate substrates. Pyrazoles are also suitable for this method, various 4-halopyrazoles derivatives were obtained by using N-halosuccinimide (NXS) as the halogen source.
Fu, Lili,Bao, Xiaodong,Li, Shanshan,Wang, Lingtian,Liu, Zhiguo,Chen, Wanzhi,Xia, Qinqin,Liang, Guang
p. 2504 - 2511
(2017/04/03)

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.
Madabhushi, Sridhar,Jillella, Raveendra,Sriramoju, Vinodkumar,Singh, Rajpal
supporting information
p. 3125 - 3131
(2014/06/10)

Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides
The reaction of aromatic or benzylic disulfides with 2.5 equiv of Selectfluor in acetonitrile/water (10:1) at room temperature efficiently produced the corresponding thiosulfonates. Conversely, the reaction of disulfides with 6.5 equiv of Selectfluor or thiosulfonates with 4.5 equiv of Selectfluor in refluxing acetonitrile/water (10:1) provided sulfonyl fluorides in high yields. Accufluor and FP-T300 are also effective in preparing sulfonyl fluorides from disulfides under the similar reaction conditions. Sulfonyl chlorides or sulfonyl bromides were effectively obtained from the reaction of disulfides with 6 equiv of either N-chlorosuccinimide or N-bromosuccinimide in acetonitrile/water (10:1) at room temperature. Some other electrophilic chlorinating or brominating reagents are also able to be used instead of N-chlorosuccinimide or N-bromosuccinimide for the syntheses of sulfonyl halides from disulfides. These reactions of disulfides with electrophilic halogenating reagents are convenient methods to prepare thiosulfonates and sulfonyl halides.
Kirihara, Masayuki,Naito, Sayuri,Nishimura, Yuki,Ishizuka, Yuki,Iwai, Toshiaki,Takeuchi, Haruka,Ogata, Tomomi,Hanai, Honoka,Kinoshita, Yukari,Kishida, Mari,Yamazaki, Kento,Noguchi, Takuya,Yamashoji, Shiro
p. 2464 - 2471
(2014/04/03)

PROCESS FOR PRODUCING 3-CHLOROMETHYL-3-CEPHEM DERIVATIVE
An industrially advantageous process for producing 3-chloromethyl-3-cephem derivative crystals. The process for 3-chloromethyl-3-cephem derivative production comprises: a first step in which a thiazolineazetidinone derivative (1) is reacted with a sulfonyl halide (2) in the presence of an acid in a solvent to obtain an azetidinone derivative (3); a second step in which the azetidinone derivative (3) is reacted with a chlorinating agent in an organic solvent to obtain a chlorinated azetidinone derivative (4); and a third step in which the chlorinated azetidinone derivative (4) is reacted with an alcoholate (5) at a pH of 8 or lower in a solvent comprising an alcohol and an ether and a 3-chloromethyl-3-cephem derivative (6) is recovered in the form of crystals.
-
Page/Page column 22; 23

(2008/06/13)

Preparation of sulfonamides from sodium sulfonates: Ph3P·Br2 and Ph3P·Cl2 as a mild halogenating reagent for sulfonyl bromides and sulfonyl chlorides
Arene- and alkanesulfonamides were prepared by treatment of the corresponding sodium sulfonates with triphenylphosphine dibromide or dichloride followed by amines in the presence of triethylamine via sulfonyl halides. Reactions of sodium aminosulfonates gave cyclized products. Amidation of p-toluenesulfonic acid with triphenylphosphine dichloride was also examined to give N-benzyl-p-toluenesulfonamide. Methyl p- toluenesulfonate was obtained by esterification of sodium p-toluenesulfonate via p-toluenesulfonyl chloride.
Kataoka, Tadashi,Iwama, Tetsuo,Setta, Tomofumi,Takagi, Atsuko
p. 423 - 426
(2007/10/03)

A Convenient Conversion of Primary Amines into the Corresponding Halides Radical Promoted Halodeamination via N-Substituted-N-Tosylhydrazines
Treatment of 1-substituted-1-tosylhydrazines with 2 equivalents of NCS or NBS in dry THF in presence of light affords the corresponding alkyl halides in good yields.This reaction presumably involves the initial formation of a stabilized hydrazyl radical which is halogenated in a radical chain process.Elimination of p-toluenesulfinic acid and extrusion of nitrogen leads to the corresponding alkyl halide.This route provides an improved method for halodeamination under neutral reaction conditions.
Collazo, Luis R.,Guziec, Frank S.,Hu, Wei-Xiao Jr.,Pankayatselvan, Ratnadevi
p. 7911 - 7914
(2007/10/02)

Preparation and Reactions of Some Cyclic Orthoester Derivatives
Deprotonation of the alkoxysulphone (5) followed by quenching with diphenyl disulphide yields the dithioorthoester (6) and not the expected ketene monothioacetal (7).Attempts at orthoester exchange of (6) with decanol with a variety of reagents lead to ring opened products.Quenching of the anion derived from (5) with sulphuryl chloride or bromine leads respectively to the chloride (19) and bromide (20).Solvolysis of these halides leads to formation of sulphinate esters.
Crich, David,Ritchie, Timothy J.
p. 2319 - 2328
(2007/10/02)

REACTIONS OF SULFOHYDRAZIDES WITH BENZENESELENIC ACID, SELENIUM HALIDES, AND SULFUR HALIDES. A CONVENIENT PREPARATION OF SELENOSULFONATES AND THIOSULFONATES
The oxidation of sulfohydrazides with benzeneselenic acid provides an efficient and convenient preparation of selenosulfonates.Se-Phenyl p-tolueneselenosulfonates was also produced in good to excellent yield from the reaction of p-toluenesulfohydrazide with PhSeCl, PhSeBr, or PhSeCl3.Sulfohydrazide react with sulfenyl halides or with PhSBr3 to produce thiosulfonates generally high yield.The treatment of p-toluenesulfohydrazide with benzenetellurinic acid, PhTeCl3, or PhTeBr3, afforded only diphenyl ditelluride and not the corresponding tellerosulfonate.
Back, Thomas G.,Collins, Scott,Krishna, M. Vijaya
p. 38 - 42
(2007/10/02)

OXIDATION OF N-ALKYL-N'-TOSYLHYDRAZINES WITH BROMINE
Oxidation of N-alkyl-N'-tosylhydrazines with bromine yield alkyl bromides, vicinal alkyl dibromides and traces of alcohols.The main products of primary hydrazines are monobromides whereas secondary hydrazines preferably produce dibromides.The reaction proceeds with evolution of nitrogen and hydrobromic acid and by the formation of intermediate sulfinic ester wich may be isolated.Various substrates were examined under different conditions to confirm the validity of the reaction mechanism hypothesized.
Palmieri, Gianni
p. 4097 - 4102
(2007/10/02)

Bromonitromethane, a Versatile Electrophile: Reactions with Feebly Basic Nucleophiles
Bromonitromethane reacts with feebly basic sulphur, phosphorus, and halogen nucleophiles at bromine or at carbon; the anion of bromonitromethane reacts with tributylboron to give 1-nitropentane.
Fishwick, Brian R.,Rowles, David K.,Stirling, Charles J. M.
p. 835 - 836
(2007/10/02)