14933-91-6Relevant academic research and scientific papers
Flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines
Jiang, Xinpeng,Shen, Zhifeng,Zheng, Cong,Fang, Liyun,Chen, Keda,Yu, Chuanming
supporting information, (2020/07/24)
A flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines with thiols under mild reaction conditions is presented for the first time. This metal-free reaction provides an atom-economic pathway to prepare various aryl sulfides with outstanding functional group compatibility. Moreover, it consumes molecular oxygen as the only terminal oxidant and produces environmentally-friendly H2O as the only byproduct.
Silver ion mediated in situ synthesis of mixed diaryl sulfides from diaryl disulfides
Gogoi, Prasanta,Gogoi, Sandhya R.,Kalita, Mukul,Barman, Pranjit
, p. 873 - 877 (2013/05/21)
The AgNO3-mediated in situ scission of aromatic disulfides in the presence of electron-rich aromatic compounds results in the efficient synthesis of diaryl sulfides. Key features of this new methodology are high yields of aromatic and heteroaromatic sulfides, mild reaction conditions, simplicity, simple workup, and avoiding foul-smelling reactants like thiols. Georg Thieme Verlag Stuttgart · New York.
Imination of sulfur-containing compounds: XXXVI. A new method of synthesis and oxidative arylsulfonylimination of sulfenamides
Koval'
, p. 386 - 389 (2007/10/03)
Sulfenylation of ammonia, amines, and arenesulfonamide sodium salts with N-(arylsulfenyl)-N,N′-bis(arylsulfonyl)sulfinimidamides afforded unsubstituted and N-substituted arenesulfenamides. Oxidation of the latter with N-chloro sulfonamide sodium salts gav
A new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine, and its optically active version
Tanaka,Azuma,Fang,Uchida,Iwata,Ishida,In,Maezaki
, p. 33 - 36 (2007/10/03)
We have developed a new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine 3, that is readily available and stable upon storage. Compound 3 easily reacts with amines or thiols to give the corresponding sulfenamides or asymmetrical disulfides in excellent yields. It was also found that the α-sulfenylation reaction of carbonyl compounds with 3 proceeds smoothly. Furthermore, optically active 4-diphenylmethyl derivative 4 was synthesized as an asymmetric sulfenylation reagent, which realized 96% e.e. upon α-sulfenylation of a cyclic β-keto ester.
Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides
Makosza, Mieczyslaw,Bialecki, Maciej
, p. 4878 - 4888 (2007/10/03)
A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.
N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides
Barton, Derek H. R.,Ferreira, J. Albert
, p. 9347 - 9366 (2007/10/03)
The reaction between an acyl derivative of N-hydroxypyridine-2(1H)- thione (a Barton PTOC ester) and either an amine (primary or secondary), or the corresponding sulfenamide, led to the formation of a carboxamide in a clean transformation requiring minimal work-up and purification. The reaction with a sulfenamide is particularly useful since the only by-product, an unsymmetrical disulfide, is of both synthetic and biological value. In sterically demanding cases, Barton PTOC esters were more reactive towards benzenesulfenamides than to the corresponding free amines.
ON THE MECHANISM OF THE REACTION OF NITROSOBENZENES WITH BENZENETHIOL: THE INTERMEDIACY OF AMINOXYLS AND THEIR DEOXYGENATION
Alberti, Angelo,Benaglia, Massimo,Carloni, Patricia,Greci, Lucedio,Stipa, Pierluigi,et al.
, p. 555 - 562 (2007/10/02)
The reaction of benzenethiol with several substituted nitrosobenzenes carried out inside the cavity of an EPR spectrometer evidences the formation of adducts through the detection of the corresponding thionitroxides.The macroscale reaction of benzenethiol with nitrosobenzene confirmed the formation of the adduct and clarified the nature of the intermediates.The formation of azoxybenzene, aniline and nitrobenzene shows that an electron-transfer process between nitrosobenzene and benzenethiol is in competition with nucleophylic addition of the latter to the former compound.The identification of S-phenylbenzenethiosulphinate as well as the isolation of compound 9, bearing a sulphinyl group on a benzene ring, implies the formation of a sulphinyl radical, which is considered to be responsible for the formation of the sulphinylamide.The formation of the sulpheneamide, the main reaction product, is attributed to the interaction of thiyl radicals with the intermediate thionitroxides.The crystal structure of S-methyl-S-phenyl-N-(o-sulphonylphenyl)benzenesulphilimine, the unexpected product of the methylation of compound 9, is also described.
SULFENAMIDES AND SULFINAMIDES VIII. THE CHROMATOGRAPHY OF ARYL SULFENAMIDES
Chan, Christopher,Cole, Edward R.,Southwell-Keely, Peter T.
, p. 63 - 74 (2007/10/02)
Substituent effects with respect to position and extent of substitution in a series of N-aryl benzenesulfenamides (ArSNHAr') have been examined over several chromatographic systems.In normal phase TLC, although methyl substitution in either ring leads to
N3-(ARYLTHIO-, ARALKYLTHIO- AND ALKYLTHIO)-5,5-DIMETHYLHYDANTOINS: SULFENYL GROUP TRANSFER REACTIONS AND THEIR PROPERTIES
Takeda, Ken'ichi,Horiki, Kusuo
, p. 367 - 373 (2007/10/02)
Sulfenyl-transfer reactions toward a variety of nucleophiles were successfully carried out using N3-sulfenyl-substituted 5,5-dimethylhydantoins (2a-c).During the course of the synthesis of 2 by the reaction of N1-bromo-5,5-dimethylhydantoin (1c) with disulfides, the sulfenyl groups were found to be at the position of N3 although the bromine was at N1 in the starting monobromohydantoin (1c).Some mechanistic speculations were considered for the formation of 2 from 1c.
SULFENAMIDES AND SULFINAMIDES III. CONJUGATIVE AFFINITY AND pKa VALUES OF ARYL SULFENAMIDES
Bayfield, Raymond F.,Cole, Edward R.
, p. 237 - 242 (2007/10/02)
Relationships are discussed between the pKa values determined spectroscopically in aqueous media and the conjugative affinity of the sulfur atom in transmitting substituent effects in a series of aryl sulfenamides. - Key words: Sulfenamides; pKa values; c
