Synthesis of Binaphthol-Derived Podands Based on Selective, Acid-Promoted Reaction of Benzylic Alcohols with Ethylene Glycols

Hovorka, Martin; Stibor, Ivan; Ščigel, Radim; Smíšková, Ivana

doi:10.1055/s-1995-4926

Cited by 6 publications

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“…334,335 Clearly, the specific aim of these studies is related to selectivity, but ecological concepts also have to be considered. Their interest as additives for fuels was reported later from aliphatic alcohols by a homogeneous or heterogeneous acid catalysis.…”

Section: Glycerol Ether Synthesis Via Acid Catalysismentioning

confidence: 99%

“…In the 1990s, the etherification of activated alcohols in acidic media with glycols or glycerol was described in order to functionalize bioactive molecules (antitumor agents, for example) in order to increase their solubility in water. , Clearly, the specific aim of these studies is related to selectivity, but ecological concepts also have to be considered. Their interest as additives for fuels was reported later from aliphatic alcohols by a homogeneous or heterogeneous acid catalysis. , …”

Section: From Glycerol By a Direct One-step Synthesismentioning

confidence: 99%

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Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies

et al. 2015

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Section: Glycerol Ether Synthesis Via Acid Catalysismentioning

confidence: 99%

Section: From Glycerol By a Direct One-step Synthesismentioning

confidence: 99%

Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies

et al. 2015

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Molecular recognition of amino acid esters in liquid polymeric membrane ion-selective electrodes

Kronďák

Shishkanova

Holakovský

et al. 2001

Analytica Chimica Acta

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Synthesis, Resolution, and Determination of Absolute Configuration of a Vaulted 2,2‘-Binaphthol and a Vaulted 3,3‘-Biphenanthrol (VAPOL)

et al. 1996

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Two methods for the synthesis of vaulted biaryls were developed involving the reactions of carbene complexes with alkynes and the [2 + 2] cycloaddition of ketenes. The final step in the synthesis of 3,3‘-diphenyl-[2,2‘-binaphthalene]-1,1‘-diol (39) and 2,2‘-diphenyl-[3,3‘-biphenanthrene]-4,4‘-diol (47) (VAPOL) was phenol coupling of the 3-phenyl-1-naphthol (14) and the 2-phenyl-4-phenanthrol (28), respectively. The naphthol 14 could be prepared from the thermolysis of phenylacetyl chloride in the presence of phenylacetylene or from the benzannulation of the pentacarbonyl(phenylmethoxymethylene)chromium(0) (15) with phenylacetylene which upon an acetylative workup gives O-acetyl-4-methoxy-2-phenyl-1-naphthol (16). The reductive cleavage of the acetoxy group in 16 was unexpectedly affected by aluminum chloride and ethanethiol which were used to cleave the methyl ether. In a similar manner, the phenanthrol 28 could either be prepared from the 1-naphthylacetyl chloride (30) or pentacarbonyl(1-naphthylmethoxymethylene)chromium(0) (21). A new procedure for the preparation of carbene complexes was developed utilizing dimethyl sulfate as methylating agent. Unlike the benzannulation of the phenyl complex 15, the benzannulation of the naphthylcarbene complex 21 with phenylacetylene gave a side product which resulted from the incorporation of 2 equiv of the alkyne. This side product could be minimized by the proper control of the concentration of the alkyne. The phenol coupling of the 3-phenyl-1-naphthol with ferric chloride gave 2,2‘-diphenyl-[2,2‘-binaphthalene]-4,4‘-diol (38) and with air as oxidant gave the of 3,3‘-diphenyl-[2,2‘-binaphthalene]-1,1‘-diol (39). Oxidative coupling of the 2-phenyl-4-phenanthrol (28) with air gave 2,2‘-diphenyl-[3,3‘-biphenanthrene]-4,4‘-diol (47) (VAPOL), but the same coupling with 2-tert-butyl-4-phenanthrol (34) failed. The 2,2‘-binaphthol 39 was resolved via its cyclic diester with phosphoric acid by salt formation with (−)-brucine, and the 3,3‘-biphenanthrol 47 was resolved via its cyclic deiester with phosphoric acid (49) by salt formation with (−)-cinchonidine. The configuration of (−)-39 was shown to be S from an X-ray analysis of the brucine salt, and the configuration of (+)-47 was shown to be S from an X-ray analysis the amide (S,S)-54 derived from 49 and (S)-α-methylbenzylamine.

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Synthesis of Binaphthol-Derived Podands Based on Selective, Acid-Promoted Reaction of Benzylic Alcohols with Ethylene Glycols

Cited by 6 publications

References 0 publications

Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies

Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies

Molecular recognition of amino acid esters in liquid polymeric membrane ion-selective electrodes

Synthesis, Resolution, and Determination of Absolute Configuration of a Vaulted 2,2‘-Binaphthol and a Vaulted 3,3‘-Biphenanthrol (VAPOL)

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