79999-62-5

Upstream product

• 79999-60-3 2,5-dihydro-2,2-diphenyl-1,3,4-thiadiazole 
• 1450-31-3 Thiobenzophenon 

Downstream Products

• 79999-66-9 2,2-diphenylthiolane-3,4-cis-dicarboxylic anhydride 
• 88691-99-0 4-methylthio-4-(1-naphthyl)-5,5-diphenyl-1,3-dithiolane 
• 79999-64-7 5,5'-diphenylspiro[xanthene-9,4'-[1,3]dithiolane] 
• 88691-96-7 5,5'-diphenylspiro[thioxanthene-9,4'-[1,3]dithiolane] 
• 88691-98-9 5,5-diphenyl-4,2'-spirobis[1,3-dithiolane]-4',5'-dione 
• 79999-69-2 2,2-diphenylthiolane-3,3,4,4-tetracarbonitrile 
• 79999-61-4 2,2,3,3-tetraphenyl-1,4-dithiane 
• 88692-10-8 methyl 2,5-dihydro-2,2-diphenyl-thiophene-3-carboxylate 
• 88692-03-9 tetramethyl 2,2-diphenylthiolane-3,3,4,4-tetracarboxylate 
• 100281-70-7 2,2,4,4-tetramethyl-5',5'-diphenylspiro[cyclobutane-3,4'-[1,3]dithiolane]-1-one 
• 89547-08-0 3-(4-Nitro-phenyl)-2,2-diphenyl-2,3-dihydro-[1,3,4]thiadiazole 
• 2675-31-2 benzophenone-(4-nitro-phenylhydrazone) 
• 88692-01-7 dimethyl 2,2-diphenylthiolane-3,4-cis-dicarboxylate 
• 79999-63-6 dimethyl 2,2-diphenyl-1,3,4-thiadiazolidine-3,4-dicarboxylate 

Relevant academic research and scientific papers

Synthesis of ferrocenyl-substituted 1,3-dithiolanes via [3 + 2]-cycloadditions of ferrocenyl hetaryl thioketones with thiocarbonyl S-methanides

Ferrocenyl hetaryl thioketones react smoothly with in situ generated thiocarbonyl S-methanides to give 1,3-dithiolanes. In the case of aromatic S-methanides, the sterically more crowded 4,4,5,5-tetrasubstituted 1,3-dithiolanes (2-CH2 isomers) w

Strong influence of the trifluoromethyl group on the chemoselectivity of [3+2]-cycloadditions of thiocarbonyl S-methanides with α,β-unsaturated ketones

The in situ-generated reactive thiocarbonyl S-methanides were reacted with fluorinated enones. The type of the obtained [3+2]-cycloadduct depends strongly on the location of the activating CF3group. In the case of enones containing the CF3

1,3-Dipolar cycloadditions, 116. The formation of 1,3-dithiolanes from aromatic thioketones and diazomethane - The mechanism of the Schonberg Reaction

Reactions of diaryl thioketones with diazomethane at room temperature afford 4,4,5,5-tetraaryl-1,3-dithiolanes; the scope of this surprising 2:1 interaction has been studied for decades (Schonberg Reaction). The clue to the mechanism was our observation that the stoichiometry is 1:1 at -78 °C, and 2,5-dihydro-2,2-diaryl-1,3,4-thiadiazoles are formed as primary [2+3] cycloadducts. They lose N2 at -45 °C in first-order reactions generating diaryl thioketone S-methylides which can be intercepted by thioketones (→1,3-dithiolanes), multiple CC bonds, or acids HX. In the absence of trapping reagents, the elusive intermediates either dimerize furnishing 2,2,3,3-tetraaryl-1,4-dithianes or give rise to 2,2-diaryl-thiiranes by electrocyclization. Beyond thiobenzophenone and diazomethane, our main model reaction, the studies involve fluorene-9-thione, 4,4-dimethoxy- and 4,4- dichloro-thiobenzophenone. The ring of 2,5-dihydro-2,2-diphenyl-1,3,4- thiadiazole (8) is opened by LDA at -78 °C and derivatives of anion 12 are obtained. - In summa: The Schonberg reaction consists of two 1,3-dipolar cycloadditions, linked by a 1,3-dipolar cycloreversion.

NEW THIOCARBONYL YLIDES FROM THIOBENZOPHENONE

Thiobenzophenone is converted to 1,3,4-thiadiazolines by reaction with diazoethane, phenyldiazomethane or diphenyldiazomethane at -78 deg C.Extrusion of nitrogen from the thiadiazolines furnishes thiocarbonyl ylides which, in turn, undergo electrocyclic r