In 2010,Angewandte Chemie, International Edition included an article by Liu, Taifeng; Liu, Yan; Xuan, Weimin; Cui, Yong. Application In Synthesis of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol. The article was titled 《Chiral nanoscale metal-organic tetrahedral cages: diastereoselective self-assembly and enantioselective separation》. The information in the text is summarized as follows:
Chiral atropisomeric 1,1′-biphenyl-3,3-diyl-bridged 1,3-diketones and their iron(III) and gallium complexes undergo self-assembly yielding tetrahedral homochiral clusters possessing chiral cavity; alcs. were resolved by formation of host-guest compounds with the iron(III) cluster tris-diketonate. Diacetylation of (1S)- and (1R)-5,5′,6,6′-tetramethyl-2,2′-(OMOM)2-1,1′-biphenyl-3,3′-dicarboxaldehyde [3,3′-Q(CHO)2] by biacetyl-trimethyl phosphite complex gave the enantiopure bis-diketonate proligands, 3,3′-Q[CH(COMe)2]2. These ligands were reacted with FeCl3 and GaCl3 giving the corresponding tetrameric nanoscale complex hosts, [Fe[3,3′-Q[C(COMe)2]2]3]4 (1) and [Ga[3,3′-Q[C(COMe)2]2]3]4 (2), composed from homochiral ΔΔΔΔ- or ΛΛΛΛ-units, for ligands (1R)- and (1S)-3,3′-Q[CH(COMe)2]2, resp. Inclusion of racemic 2-butanol and 3-methyl-2-butanol into chiral cavity of (1S)-1 with subsequent desorption gave the corresponding resolved alcs. with >99% ee. After reading the article, we found that the author used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Application In Synthesis of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)
(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Application In Synthesis of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol
Referemce:
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Alcohols – Chemistry LibreTexts