73732-23-7Relevant academic research and scientific papers
Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light
Fu, Ying,Wu, Qing-Kui,Du, Zhengyin
supporting information, p. 1896 - 1900 (2021/04/06)
An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.
Electrochemical Coupling of Arylsulfonyl Hydrazides and Tertiary Amines for the Synthesis of β-Amidovinyl Sulfones
Kim, Han-Sung,Lee, Sunwoo
, p. 6951 - 6955 (2019/11/13)
The reaction of arylsulfonyl hydrazides with tertiary amines provided β-amidovinyl sulfones in good yields under mild electrochemical conditions. The reactions were carried out using an acid, in a solution of nBu4NBF4 in dimethyl sulfoxide in undivided cells with graphite-platinum electrodes under a constant current. The arylsulfonyl hydrazides and tertiary amines were activated via a radical process by electrochemical oxidation and reacted to give the desired β-amidovinyl sulfones.
Charge-Transfer Complex Promoted Regiospecific C?N Bond Cleavage of Vicinal Tertiary Diamines
Fu, Ying,Xu, Qin-Shan,Shi, Chun-Zhao,Du, Zhengyin,Xiao, Caiqin
supporting information, p. 3502 - 3506 (2018/09/14)
A catalyst-free, charge-transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C?N bond cleavage of vicinal tertiary diamines. (Figure presented.).
One-Pot synthesis of sulfonamides from primary and secondary amine derived sulfonate salts using cyanuric chloride
Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Asrari, Zeinab,Behrouz, Somayeh,Amini, Zohreh,Behrouz, Marzieh
experimental part, p. 3983 - 3988 (2010/03/26)
A convenient, mild and efficient one-pot synthesis of new sulfonamides is described. The reaction of primary or secondary amine derived sulfonate salts in the presence of cyanuric chloride, triethylamine as base, and anhydrous acetonitrile as solvent at room temperature gives the corresponding sulfonamides in good to excellent yields. Georg Thieme Verlag Stuttgart.
Reactivity of cage-like amines toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile
Sadovskii,Solomoichenko,Kas'yan,Golodaeva,Anikanova,Kas'yan,Savelova
, p. 50 - 56 (2007/10/03)
The nucleophilic reactivity of amines of the norbornane, norbornene, and adamantane series toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile at 25°C is determined mainly by the steric factor. Parameters characterizing spatial accessibility of the reaction center in the amine molecule have been determined. Cage-like substituents show no appreciable effect on the amine reactivity, as compared to common alkyl groups.
NUCLEOPHILIC SUBSTITUTION AT SULFONYL SULFUR ATOM : AMINOLYSIS OF 1-TOSYL-3-METHYL IMIDAZOLIUM CHLORIDE IN AQUEOUS MEDIUM.
Monjoint, Pierre,Ruasse, Marie-Francoise
, p. 3183 - 3186 (2007/10/02)
Kinetics of the reaction of 1-tosyl-3-methyl-imidazolium chloride with various amines were measured to examine the nature of sulfonyl transfer in enzymatic reactions.The activations parameters and the value of the Broensted exponent, β=0.48, are consistent with a small degree of bonding between the entering amine and the sulfur atom in the transition state.Similarities in the nucleophilic behavior of sulfonyl and carbonyl groups are detected.
