102555-71-5Relevant articles and documents
Synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2, 2′-disulfonic acids
Hatano, Manabu,Sugiura, Yoshihiro,Ishihara, Kazuaki
, p. 1311 - 1314 (2010)
A convenient synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2,2′-disulfonic acids (BINSA, 1) was developed. The key was directed ortho-lithiation of BINSA methyl ester 2 with n-BuLi and subsequent reaction with an electrophile. Electrophiles such as Br2, I2, Me3SiOTf, and i-PrOB(Pin) reacted smoothly with 3,3′-dilithiated BINSA methyl ester, and the corresponding 3,3′-dihalo-, 3,3′-bis(trimethylsilyl)-, and 3,3′-diboryl- BINSA derivatives were obtained in yields of 21-78%. This simple synthetic method is highly attractive since the ability to prepare 3,3′- disubstituted BINOLs in advance can be useful.
A useful sulfur-transfer reaction with tetrathiomolybdate: Conversion of arylamines to aryl disulfides
Bhar,Chandrasekaran
, p. 785 - 786 (1994)
A convenient method for the synthesis of a series of symmetrical aryl disulfides from arylamines via the reaction of their stable diazonium salts with tetrathiomolybdate under anhydrous conditions is described.
ASYMMETRIC OXIDATION OF THIOETHERS. OPTICAL RESOLUTION OF -2,2'-DITHIOL
Furia, Fulvio Di,Licini, Giulia,Modena, Giorgio,Lucchi, Ottorino De
, p. 2575 - 2576 (1989)
Almost optically pure (e.e.>98percent) -2,2'-dithiol (2) is obtained by resolution of racemic 2 via the transformation of the sulfidryl functions into the corresponding thioethers 3 which are asymmetrically oxidized to diastereomeric chiral monosulfoxides 4 and then reconverted into 2.The diastereo and enantioselectivity is dependent on the structure of the thioether; i.e. the dimethylthioether 3a gives two diastereomeric sulfoxides 4a in ca. 1:1 ratio, each of them in >98percent e.e., while cyclic dithioethers 3b-d afford a single diastereomeric sulfoxide 4b-d in 46-78percent e.e..
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
Bandarage, Upul K.,Simpson, Jim,Smith, Robin A. J.,Weavers, Rex T.
, p. 3463 - 3472 (1994)
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.
Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol
Brégent, Thibaud,Bouillon, Jean-Philippe,Poisson, Thomas
supporting information, p. 13966 - 13970 (2021/08/25)
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.
PROCESS FOR PRODUCTION OF DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALYST, PROCESS FOR PRODUCTION OF -AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE SALT
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Page/Page column 7, (2010/08/07)
Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1'-binaphthyl-2,2'-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80°C for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1'-binaphthyl-2,2'-disulfonate. The (R)-1,1'-binaphthyl-2,2'-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH2Cl2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0°C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0°C for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.
