19721-97-2Relevant academic research and scientific papers
Solvent-Driven Mono- and Bis-sulfenylation of (E)-β-Iodovinyl Sulfones with Thiols for Flexible Synthesis of 1,2-Thiosulfonylalkenes and 1,2-Dithioalkenes
Reddy, Raju Jannapu,Kumari, Arram Haritha,Sharadha, Nunavath,Krishna, Gamidi Rama
, p. 3934 - 3951 (2022/03/16)
The nature of solvent is a key factor for stereoselective mono- and bis-thiolation of (E)-β-iodovinyl sulfones with thiols under basic conditions. A novel and unprecedented vicinal bisthiolation of (E)-β-iodovinyl sulfones with thiols under the influence of K2CO3/DMSO at room temperature for quick assembly of (E)-1,2-dithio-1-alkenes is presented. Solvent-induced stereoselective monosulfenylation of (E)-β-iodovinyl sulfones with thiols has also been established for the synthesis of both (E)- and (Z)-1,2-thiosulfonylethenes in MeCN and MeOH, respectively. Moreover, K2CO3-mediated desulfonylative-sulfenylation of (Z)-1,2-thiosulfonylethenes with thiols in DMSO furnished unsymmetrical (Z)-1,2-dithio-1-alkenes for the first time. The solvent-dependent versatile reactivity of (E)-β-iodovinyl sulfones has been successfully explored to provide a set of (E)-/(Z)-1,2-dithio-1-alkenes and (E)-/(Z)-1,2-thiosulfonyl-1-alkenes in good to high yields with excellent stereoselectivities. Notably, this operationally simple process utilizes a broad substrate scope with good functional group tolerance and compatibility. The efficacy of the process has been proven for gram-scale reactions, and plausible mechanistic models are outlined on the basis of experimental results and control experiments.
Geometrical Isomerism in Unsaturated Sulphide-Sulphones and Disulphones: Part IV - Synthesis and Configurational Studies of E-aM, E-M and Z-M Isomers of Some Thio and Sulphonyl Substituted p-Tolylsulphonylstyrenes
Naidu, M. S. R.,Prabhakara, R.
, p. 140 - 145 (2007/10/02)
A series of (E)-aM-β-alkylthio- or arylthio-α-p-tolylsulphonylstyrene (4a-f) and (E)-M- and (Z)-M-α-alkylthio- or arylthio-β-p-tolylsulphonylstyrenes (5a-f and 6a-f) have been synthesized by the nucleophilic displacement of halogens with sodium salts of v
