33839-73-5

Upstream product

• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 86201-64-1 2-phenyl-1,3-dithian-2-ylium tetrafluoroborate 
• 100-52-7 benzaldehyde 

Downstream Products

• 134-81-6 benzil 

Relevant academic research and scientific papers

Influence of an oxidising impurity on preparation of 2-lithio-1,3-dithiane: Isolation of bis[2-(1,3-dithianyl)]methanol

Bis-dithianylalkanols and dimers are formed in preparation of 2-lithio-1,3-dithianes due to the presence of oxidising impurity in n-BuLi (perhaps n-BuOOLi).

Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes

The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.

Rotational isomerism and crystal structures of 2,2′-diphenyl-2,2′-bi-1,3-dithianyl and 2,2′-diphenyl-2,2′-bi-1,3-dioxolanyl

Dipole moments of the compounds 2,2′-diphenyl-2,2′-bi-1,3-dithianyl 1 and 2,2′-diphenyl-2,2′-bi-1,3-dioxolanyl 2 in carbon tetrachloride and benzene have been measured over a range of temperatures. The crystal and molecular structures of the compounds were determined by single-crystal X-ray diffraction methods. Analyses of the crystal structures and relative permittivity data show that the compounds exist in the trans conformation in the solid state and as rotameric mixtures in solution with a predominantly high trans population of 85% and 80% respectively at 25°C. The experimentally derived values of the energy difference between the gauche and trans rotamers and the gauche/trans population quotients were compared with the values predicted by molecular orbital calculations.

1,3-Dithienium and 1,3-Dithiolenium Salts. IX. Reactions of 1,3-Dithiane-2-ylium Tetrafluoroborates with C-Nucleophiles

1,3-Dithian-2-ylium tetrafluoroborates (1), which can be easily obtained by variable methods, react in good to excellent yields with variable C-nucleophiles to new geminal disubstituted 1,3-dithianes. The latter compounds are potential precursors of inter

Reactions of 1,3-Dithiolan-2-ylium and 1,3-Dithian-2-ylium Tetrafluoroborates and Ambident 2-Styryl Derivatives

The ambident 2-styryl-1,3-dithiolan-2-ylium and 2-styryl-1,3-dithian-2-ylium cations react with preferential carbon-carbon bond formation at the β ethylenic carbon when treated with methylmagnesium iodide.In the lithium aluminium hydride reaction, reduction occurs at either electrophilic carbon center.Methanol and thiophenol react selectively with the β carbon of the side chain.The adduct formation with the heteroatom nucleophiles is readily reversed by acid catalysis.In the absence of the styryl group, the nucleophilic addition is at C-2.Dithioketals of symmetric 1,2-divarbonyl derivatives are readily formed by zinc-induced reductive dimerization of 1,3-dithiolan- and 1,3-dithian-2-ylium salts.