133286-28-9

Upstream product

• 133286-19-8 (E)-5-(4-Chloro-phenyl)-2-[1,3]dithiolan-2-ylidene-3-oxo-pent-4-enoic acid 
• 6784-59-4 1-(1,3-dithiolan-2-ylidene)propan-2-one 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 1610888-96-4 (E)-1-(4-chlorophenyl)-4-(1,3-dithiolan-2-ylidene)-5,5,5-trifluoropent-1-en-3-one 
• 1639790-45-6 (E)-1-(4-chlorophenyl)-4-(1,3-dithiolan-2-ylidene)hepta-1,6-dien-3-one 
• 1639790-61-6 (E)-1,6-bis(4-chlorophenyl)-4-(1,3-dithiolan-2-ylidene)hepta-1,6-dien-3-one 
• 1142319-76-3 7-(4-chlorophenyl)-10-(1,3-dithiolan-2-ylidene)-3,3-dimethylspiro[5.5]undecane-1,5,9-trione 
• 1245820-93-2 (2E,6E)-tert-butyl 7-(4-chlorophenyl)-4-(1,3-dithiolan-2-ylidene)-5-oxohepta-2,6-dienoate 

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.

Palladium-catalyzed oxidative heck-type allylation of β,β- disubstituted enones with allyl carbonates

The palladium-catalyzed oxidative Heck-type allylation of β,β-disubstituted enones, i.e., α-oxoketene dithioacetals, was efficiently realized with allyl carbonates, providing a concise route to highly functionalized dienes. The present synthetic methodology utilizes the substrate activation strategy to activate the C-H bond of β,β-disubstituted enones by introduction of a 1,2-dithiolane functionality to make the enone substrate highly polarized and thus increase its reactivity, demonstrating rare examples for transition metal-catalyzed allylic substitution of ss,ss-disubstituted enones through a Heck-type allylation process.

A novel route to alkenoyl- and cinnamoylketene dithioacetals

2-Acetyl(ethoxycarbonyl)methylene-1,3-dithietane and -dithiane (1) were condensed with various aldehydes or ketones to afford high yields of the corresponding substituted 2-(1-carboxy-2-oxo-3-butenylidene)-1,3-dithietanes and -dithianes 4, which upon heating decarboxylated smoothly to give the title compounds in high yield.