188-57-8

Upstream product

• 194-65-0 1,1'-binaphthothiophene 
• 102555-71-5 1,1'-binaphthalene-2,2'-dithiol 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 162825-40-3 (S)-4<(1''R,2''S,3''R,4''R)-1'',2'',3'',4'',5''-pentamethoxypentyl>-dinaphtho<2,1-d:1',2'-f><1,3>dithipin 
• 602-09-5 1,1'-bi-2-naphthol 
• 147923-23-7 <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) 
• 91-60-1 2-Naphthalenethiol 
• 124414-28-4 (2,2'-Dimethylthio)<1,1'-binaphthalene> 
• 124414-32-0 (2-Methylsulfinyl-2'-methylthio)<1,1'-binaphthalene> 
• 124414-28-4 (2,2'-Dimethylthio)<1,1'-binaphthalene> 
• 124414-29-5 Dinaphtho<2,1-d:1',2'-g><1,4>dithiocane 
• 124414-32-0 (2-Methylsulfinyl-2'-methylthio)<1,1'-binaphthalene> 
• 124414-28-4 (2,2'-Dimethylthio) 
• 124414-33-1 Dinaphtho<2,1-d:1',2'-f><1,4>dithiocane S-oxide 

Downstream Products

• 102555-71-5 1,1'-binaphthalene-2,2'-dithiol 
• 55441-99-1 (R)-1,1′-binaphthalene-2,2′-dithiol 
• 55441-99-1 (S)-[1,1'-binaphthalene]-2,2'-dithiol 

Relevant academic research and scientific papers

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.

A simple and efficient oxidative coupling of aromatic nuclei mediated by manganese dioxide

Oxidative intramolecular coupling of the aryl rings of various stilbenes for direct construction of the phenanthrene ring system is promoted efficiently by manganese dioxide-trifluoroacetic acid at room temperature in excellent yields. This approach is also applied to the intermolecular biaryl coupling of 2-naphthols, 2-naphthalenethiol, 2-naphthylamine, a phenol ether and a phenol under very mild conditions. An electron-transfer mechanism is proposed in which manganese dioxide acts as a two-electron oxidant.

Resolution of (1,1'-binaphthalene)-2,2'-dithiol via diastereoisomeric dithioacetals derived from D-glucose

The efficient resolution of (1,1'-binaphthalene)-2,2'-dithiol has been achieved by the preparation and separation of the chiral diastereoisomeric binaphthalene dithioacetals derived from 2,3,4,5,6-penta-O-methyl-D-glucose followed by transthioacetalization with ethane-1,2-dithiol.

Syntheses of Dibenzodiselenin and Related Novel Chalcogenide Heterocyclic Compounds

Reaction of 2,2'-dilithio-1,1'-binaphthyl with selenium followed by air oxidation gives a mixture of dinaphthoselenophene and dimer and oligomers of 2,2'-diseleno-1,1'-binaphthyl. 2,2'-Dilithio-1,1'-biphenyl reacts with selenium to afford dibenzodiselenin.Structures of the dimeric 2,2'-diseleno-1,1'-binaphthyl and dibenzodiselenin have been confirmed by X-ray crystallographic analyses.Similar reaction of 2,2'-dilithio-1,1'-binaphthyl with sulfur or tellurium gives a mixture of dinaphthothiophene and dinaphthodithiin or a mixture of dinaphthotellurophene and oligomer of 2,2'-ditelluro-1,1'-binaphthyl, respectively.Dibenzotellurophene and oligomer of 2,2'-ditelluro-1,1'-biphenyl are obtained from reaction of 2,2'-dilithio-1,1'-biphenyl with tellurium.

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

SYNTHESIS OD 1,1'-DIBENZO- AND 1,1'-DINAPHTHO-2,2'-DITHIOLS FROM THE RESPECTIVE THIOPHENES

The title compounds 1 and 2 were prepared from the respective, inexpensive and readily available thiophenes vis reaction with lithium and sulfur monochloride, followed by reduction with lithium alumoinium hydride.