92357-77-2Relevant academic research and scientific papers
Reactivity of 5-(Alkynyl)dibenzothiophenium Salts: Synthesis of Diynes, Vinyl Sulfones, and Phenanthrenes
Kafuta, Kevin,Rugen, Christian J.,Heilmann, Tobias,Liu, Tianshu,Golz, Christopher,Alcarazo, Manuel
, p. 4038 - 4048 (2021/05/10)
The reactivity of 5-(alkynyl)dibenzothiophenium salts 1 is explored in the presence of different nucleophiles, dienes, and under photochemical conditions. Reaction with lithium acetylides affords diynes in moderate yields; while depending on the substitution pattern, the reaction with sulfinates delivers either the alkyne transfer products, alkynyl sulfones, or β-(sulfonium) vinyl sulfones through addition to the C?C triple bond. Similar behavior is observed when tosylamines are used as nucleophiles. Salts of general formula 1 also react with dienes to render the corresponding Diels-Alder cycloadducts. The vinyl sulfonium salts obtained by these routes further react with nucleophiles through a Michael addition, dibenzothiophene elimination sequence. Alternatively, they also engage in photoinduced radical cyclizations to produce substituted phenanthrenes. Attempts to use this specific addition/radical cyclization sequence for the construction of the 6a,7-dehydroaporphine skeleton present in several families of alkaloids are also described.
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
