5653-30-5

Upstream product

• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 106-93-4 ethylene dibromide 
• 15185-51-0 3-oxo-3-phenyl-dithiopropionic acid 
• 75-15-0 carbon disulfide 
• 98-86-2 acetophenone 
• 87094-78-8 (E)-2-(2-phenylethenyl)-1,3-dithiolane 
• 74440-20-3 2-(1,3-dithiolan-2-ylidene)-1-phenylbutane-1,3-dione 
• 5616-58-0 2-styryl-1,3-dithiolane 
• 104-55-2 3-phenyl-propenal 
• 14505-46-5 2-(2-Phenylethyl)-1,3-dithiolane 

Downstream Products

• 3445-76-9 5-phenyl-3H-1,2-dithiole-3-thione 
• 3592-47-0 Benzaldehyde-d 
• 74291-95-5 2,2'-(2-phenyl-1,3-propanediylidene-2-d)bis(1,3-dithiolane) 
• 140611-74-1 2-Acetoxy-1-phenyl-2-(1,3-thiolan-2-ylidene)ethanoate 
• 100-52-7 benzaldehyde 
• 74291-94-4 2,2'-(2-phenyl-1,3-propanediylidene)bis(1,3-dithiolane) 
• 540-63-6 ethane-1,2-dithiol 
• 93-55-0 1-phenyl-propan-1-one 
• 134129-41-2 2-(1,3-dithiolane-2-ylidene)-3-oxo-3-phenylpropanal 
• 1181844-52-9 2-(2-(4-chlorophenyl)-3-(1,3-dithiolan-2-ylidene)-1,3-diphenylpropylidene)-1,3-dithiolane 
• 1245820-39-6 (E)-ethyl 4-(1,3-dithiolan-2-ylidene)-5-oxo-5-phenylpent-2-enoate 
• 1351953-58-6 2-(1,3-dithiolan-2-ylidene)-1,3,5-triphenylpent-4-yn-1-one 
• 1415149-88-0 methyl 2-({5-[1-(1,3-dithiolan-2-ylidene)-2-oxo-2-phenylethyl]furan-2-yl}methyl)acrylate 
• 1415149-74-4 3-{5-[1-(1,3-dithiolan-2-ylidene)-2-oxo-2-phenylethyl]furan-2-yl}-2-(1,3-dithiolan-2-ylidene)-1-phenylpropan-1-one 

Relevant academic research and scientific papers

Copper-catalyzed trifluoromethylation of internal olefinic C-H bonds: Efficient routes to trifluoromethylated tetrasubstituted olefins and N-heterocycles

The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient CuII-catalyzed trifluoromethylation of internal olefins, that is, α-oxoketene dithioacetals, has been achieved by using Cu(OH)2 as a catalyst and TMSCF3 as a trifluoromethylating reagent. The push-pull effect from the polarized olefin substrates facilitates the internal olefinic C-H trifluoromethylation. Cyclic and acyclic dithioalkyl α-oxoketene acetals were used as the substrates and various substituents were tolerated. The internal olefinic C-H bond cleavage was not involved in the rate-determining step, and a mechanism that involves radicals is proposed based on a TEMPO-quenching experiment of the trifluoromethylation reaction. Further derivatization of the resultant CF 3 olefins led to multifunctionalized tetrasubstituted CF3 olefins and trifluoromethylated N-heterocycles.

Iron-catalyzed alkylation of α-oxo ketene dithioacetals

Iron-catalyzed alkylation of internal olefins, that is, α-oxo ketene dithioacetals, was successfully realized by using styrenes as the alkylating reagents. Highly functionalized tetrasubstituted olefins were prepared in moderate to high yields. the Partner Organisations 2014.

Synthesis of densely substituted 1,3-butadienes through acid-catalyzed alkenylations of α-oxoketene dithioacetals with aldehydes

Aldehydes were proved to be viable reagents for implementing alkenylation of α-oxoketene dithioacetals. AlCl3 was found to be the best catalyst. The established reaction opened an avenue to access densely substituted 1,3-butadiene derivatives. The obtained product bears multiple reactive sites that can be converted into various valuable molecules. (Chemical Equation Presented).

Oxidative cross-esterification of dithiolanes with alcohols through a cross-dehydrogenative coupling (CDC)/deprotection sequence

An unprecedented oxidative cross-esterification in an equimolar mixture of dithiolanes, alcohols and water through a CDC/deprotection sequence has been developed. The reaction itself features simple experimental procedures under very mild conditions and offers a new strategic protocol for the direct and efficient synthesis of structurally diverse esters.

Unexpected hydrobromic acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene dithioacetals

Hydrobromic acid was found to be a unique catalyst in C-C bond-forming reactions with ketene dithioacetals. Distinctly different from other acids (including Lewis and Bronsted acids), the remarkable catalytic performance of hydrobromic acid in catalytic a

Unexpected Formation of Benzaldehydes by the Reactions of Dithio- Acetals Derived from Cinnamaldehydes with 2,3-Dichloro-5,6-dicyano-p-benzoquinone in Aqueous Solvents

1,3-Dithianes 1, 1,3-dithiolanes 2, and diphenyl dithioacetals 3 derived from cinnamaldehydes reacted with 2,3-dichloro-5,6-dicyano-p-benzoquinone in aqueous solvents to give benzaldebydes 4. Hydride transfer from 1-3 to 2,3-dichloro-5,6-dicyano-p-benzoquinone followed by hydrolysis and oxidative carbon-carbon bond cleavage would produce benzaldehydes 4.

Oxidative removal of 1,3-dithiane protecting groups by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ)

A number of 1,3-dithianes have been efficiently converted into the parent carbonyl compounds in good yields by treatment with 1.5 equiv. of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in MeCN-H2O (9:1). The reactions of 2-aryl-substituted 1,3-dithianes bearing electron-donating groups on the benzene ring with DDQ afforded thioesters along with aldehydes. 1,3-Dithiolanes derived from aromatic aldehydes were transformed to thioesters, whereas 1,3-dithiolanes derived from aliphatic and aromatic ketones were stable under these reaction conditions. Diphenyl dithioacetals were stable except for 4-methoxy- and 3,4-dimethoxy-benzaldehyde diphenyl dithioacetals which gave the corresponding aldehydes. Selective cleavage reactions of 1,3-dithiane in the presence of 1,3-dithiolane or diphenyl dithioacetal have been investigated.

A convenient one-pot synthesis of ketene dithioacetals

An easy synthesis of ketene dithioacetals 2 and 3 by the condensation of carbon disulfide and active methylene compounds 1 with subsequent alkylation in the presence of potassium fluoride is described.