The Condensation of Polyhydric Phenols with Acetone

Fisher, C. H.; Furlong, Robert W.; Grant, M. S.

doi:10.1021/ja01296a042

J. Am. Chem. Soc.

1936

DOI: 10.1021/ja01296a042

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The Condensation of Polyhydric Phenols with Acetone

C. H. Fisher¹,

Robert W. Furlong²,

M. S. Grant³

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Cited by 10 publications

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“…Although its first synthesis (5,5′-dihydroxy substituted) can be traced back to at least as early as 1905 by Fabinyi and Széky by condensation of catechol and acetone in the presence of acid, its correct structure was not suggested until 1934 by Baker and further borne out in 1938 by Baker and McGowan . In the following years, 6,6′-TMSPINOLs with varied substituents on 5,5′- and 7,7′-positions were documented . Notably, the optical resolution of 6,6′-TMSPINOL was first achieved by Hagishita et al in 1971, in which (±)- 1b was successfully resolved by (+)-phenethylisocyanate.…”

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confidence: 99%

Chiral 3,3,3′,3′-Tetramethyl-1,1′-Spirobiindanyl Cyclopentadienyl (TMSCp) Ligands: Design, Synthesis, and Applications

Guo¹,

Pang²,

Jiang³

et al. 2023

Org. Lett.

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Chiral cyclopentadienyl (Cp) rhodium(III) are powerful catalysts for achieving asymmetric C–H activation. This paper describes the design and synthesis of a new type of chiral Cp ligand bearing a chiral 3,3,3′,3′-tetramethyl-1,1′-spirobiindanyl backbone. It features convenient synthesis, easy modification, and relatively low cost. Moreover, it holds great potential in achieving asymmetric C–H activation as exemplified by four examples examined in this work.

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mentioning

confidence: 99%

Chiral 3,3,3′,3′-Tetramethyl-1,1′-Spirobiindanyl Cyclopentadienyl (TMSCp) Ligands: Design, Synthesis, and Applications

Guo¹,

Pang²,

Jiang³

et al. 2023

Org. Lett.

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Green Chemistry Meets Asymmetric Organocatalysis: A Critical Overview on Catalysts Synthesis

2021

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Can green chemistry be the right reading key to let organocatalyst design take a step forward towards sustainable catalysis? What if the intriguing chemistry promoted by more engineered organocatalysts was carried on by using renewable and naturally occurring molecular scaffolds, or at least synthetic catalysts more respectful towards the principles of green chemistry? Within the frame of these questions, this Review will tackle the most commonly occurring organic chiral catalysts from the perspective of their synthesis rather than their employment in chemical methodologies or processes. A classification of the catalyst scaffolds based on their E factor will be provided, and the global E factor (E G factor) will be proposed as a new green chemistry metric to consider, also, the synthetic route to the catalyst within a given organocatalytic process.

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The condensation of 2,6‐dimethylphenol with glyoxal and with benzil

McGowan¹,

Anderson²,

Walker³

1964

Recl. Trav. Chim. Pays‐Bas

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1,1,2,2‐Tetrakis(4‐hydroxy‐3,5‐dimethylphenyl)ethane has been prepared by the condensation of 2,6‐dimethylphenol with glyoxal. The tetraacetate has been isolated, after acetylation, from the product of the reaction between 2,6‐dimethylphenol and α,β‐dichlorovinyl phenyl ether and the tetramethyl ether has been obtained directly from 2,6‐dimethylanisole and glyoxal sulfate. Benzil and 2,6‐dimethylphenol can be condensed to give benzoyl‐4,4′‐dihydroxy‐3,3′,5,5′‐tetramethyltritane and there is evidence that the dimethyl ether of this compound is formed when 4‐methoxy‐3,5‐dimethylbenzophenone is reduced with zinc dust in acetic acid.

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The Condensation of Polyhydric Phenols with Acetone

Cited by 10 publications

References 0 publications

Chiral 3,3,3′,3′-Tetramethyl-1,1′-Spirobiindanyl Cyclopentadienyl (TMSCp) Ligands: Design, Synthesis, and Applications

Chiral 3,3,3′,3′-Tetramethyl-1,1′-Spirobiindanyl Cyclopentadienyl (TMSCp) Ligands: Design, Synthesis, and Applications

Green Chemistry Meets Asymmetric Organocatalysis: A Critical Overview on Catalysts Synthesis

The condensation of 2,6‐dimethylphenol with glyoxal and with benzil

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