55441-97-9

Upstream product

• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 602-09-5 1,1'-bi-2-naphthol 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Downstream Products

• 194-65-0 1,1'-binaphthothiophene 
• 147923-23-7 <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) 
• 604-53-5 1,1'-bisnaphthalene 
• 348617-10-7 (S)-diphenyl(2'-phenyl-[1,1'-binaphthalen]-2-yl)phosphine 

Relevant academic research and scientific papers

Dinaphtho[2,1-b:1′,2′- d] thiophenes as high refractive index materials exploiting the potential characteristics of "dynamic thiahelicenes"

Dinaphtho[2,1-b:1′,2′-d]thiophene (DNT) is one of the "dynamic thiahelicenes"that is obtained as a racemate due to its low energy barrier for enantiomerization. A careful evaluation of both the metastable DNT film and the stable films of DNT/polymethyl methacrylate (PMMA) blends revealed that DNT has an extra-high refractive index of 1.808 at 633 nm, which is rarely achieved in organic small molecules. The fundamental factors responsible for the unusual observation of DNT were explored by comparing the properties of DNT with those of a flat-shaped dibenzothiophene (DBT) both in experiments and DFT calculations, and by analysing them using the Lorentz-Lorenz equation. It became clear that the unique properties of DNT were based on its flexible dynamic thiahelicene structure, leading to metastable film-forming ability, high compatibility with PMMA, and exhibition of an extra-high refractive index caused by dense packing in the amorphous film. Chemical modification of DNT provided new halogen-free vinyl monomers, which could be easily polymerized to form vinyl polymers with high refractive indices of 1.72-1.74, as well as film-forming ability, high thermal stability, and high transparency in the visible region. Thus, we could demonstrate that the DNT structure is a new promising candidate for organic polymeric high refractive index materials.

Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol

The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.

Practical synthetic approach to chiral sulfonimides (CSIs) - Chiral bronsted acids for organocatalysis

A general approach to the synthesis of optically pure 3,3'diaryl chiral sulfonimides (CSIs) from racemic BINOL has been developed. ortho-Lithiation is directed by the sulfonyl groups, and the resulting dihalides serve as the common precursors for the aryl-substituted CSIs.

A parallel colorimetric method for the rapid discovery and optimization of heterogeneous hydrodesulfurization catalysts

A spectrophotometric based, parallel approach to screen heterogeneous catalysts for hydrodesulfurization has been developed. The method utilizes optical changes resulting from the hydrodesulfurization of 1,1′-binaphthothiophene to 1,1′-binaphthyl to determine catalyst activity. Hydrodesulfurization of 1,1′-binaphthothiophene to 1,1′-binaphthyl results in a loss of conjugation in the binaphthyl ring system. This results in a blue shift of more than 60 nm in the UV-vis spectrum. Since only small amounts of the HDS catalyst and 1,1′-binaphthothiophene are required, a large number of catalysts may be screened simultaneously. The synthesis of the 1,1′-binaphthothiophene and conditions for HDS catalyst screening are described. Copyright

Conformational polymorphism and thermorearrangement of 2,2′-bis-O-(N,N-dimethylthiocarbamato)-1,1′-binaphthalene. A facile synthesis of 1,1′-binaphthalene-2,2′-dithiol

The title compound was found to exhibit conformational polymorphism which greatly influenced the efficiency of the thermorearrangement to 2,2′-bis-S-(N,N-dimethylthiocarbamato)-1,1′-binaphthalene. Recognition of this phenomenon has allowed a reproducible synthesis of 1,1′-binaphthalene-2,2′ dithiol.

Preparation of Enantiomerically Pure 1,1'-Binaphthalene-2,2'-diol and 1,1'-Binaphthalene-2,2'-dithiol

A practical preparation of enantiomerically pure 1,1'-binaphthalene-2,2'-diol (1) and 1,1'-binaphthalene-2,2'-dithiol (2) is reported.Enantiopure 2 is obtained from enantiopure 1 via Newman-Kwart rearrangement of the thiocarbamoyl derivative 5 under controlled reaction conditions.The enantiopure starting diol 1 was obtained by a simple and inexpensive method engaging condensation of thiophosphoryl chloride and (S)-(-)-α-methylbenzylamine in pyridine and reaction of the resulting phosphoramidate 3 with racemic binaphthol 1 to give quantitatively a 1:1 mixture of diasteroisomers 4 that were cleanly separated by a single recrystallization from a chloroform-ethanol mixture in very high yield.The procedures can be scaled up easily.

Enantioselective oxidation of thioethers. A route to the resolution of -2,2'-dithiol

A route to the resolution of racemic -2,2'-dithiol 2 is described, involving the transformation of 2 into a series of dithioethers.The latter are subjected to asymmetric oxidation to monosulfoxides by a procedure developed in our laboratory.For some of the thioethers examined the oxidation is highly diastereo- and/or enantioselective.The resolved 2 is then obtained from the optically pure monosulfoxides either by oxidation to the bis-sulfoxides followed by a Pummerer reaction or by a deoxygenation to the dithioether and subsequent reduction.In both cases enantiomerically pure 2 (e.e. > 98percent) was obtained.Keywords: enantioselective oxidation / optical resolution / thioethers / -2,2'-dithiol