The Structure of Anthracene

Fieser, Louis; Lothrop, Warren C.

doi:10.1021/ja01296a016

Cited by 20 publications

(7 citation statements)

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“…Thus, in exact parallel with 2-allyloxynaphthalene, the Claisen rearrangement of the 6-allyloxyindole (10) proceeds regioselectively. The transition state leading to intermediate (13), which retains some aromatic stabilisation, is clearly favoured over that leading to intermediate (14).…”

Section: Resultsmentioning

confidence: 99%

Regioselective Claisen rearrangements in indoles

Moody¹

1984

J. Chem. Soc., Perkin Trans. 1

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Section: Resultsmentioning

confidence: 99%

Regioselective Claisen rearrangements in indoles

Moody¹

1984

J. Chem. Soc., Perkin Trans. 1

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“…. 2-Methyl-3-hydroxybenzoic acid was prepared by heating the sodium salt of 3-aminonaphthalene-1,5-disulphonic acid in 50% (w/v) NaOH in a nickel bomb at 270°C (Fieser & Lothrop, 1936). We thank the 3M Company, St Paul, Minn., U.S.A., for making their high-pressure facilities available, and also Mr Milton Sandberg, who conducted the alkaline fusion.…”

Section: -215°cmentioning

confidence: 99%

The enzymic degradation of alkyl-substituted gentisates, maleates and malates

Hopper

Chapman

Dagley

1971

Biochemical Journal

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1. Cell-free extracts, prepared from a non-fluorescent Pseudomonas grown on m-cresol, oxidized gentisate and certain alkyl-substituted gentisates with the consumption of 1 mol of oxygen and the formation of 1 mol of pyruvate from 1 mol of substrate. 2. In addition to pyruvate, malate was formed from gentisate; citramalate was formed from 3-methylgentisate and 4-methylgentisate; 2,3-dimethylmalate was formed from 3,4-dimethylgentisate. 3. One enantiomer, d-(-)-citramalate, was formed enzymically from 3-methylgentisate, 4-methylgentisate and citraconate. l-(+)-Citramalate was formed from mesaconate by the same extracts. When examined as its dimethyl ester by gas-liquid chromatography, enzymically formed 2,3-dimethylmalate showed the same behaviour as one of the two racemates prepared from the synthetic compound. 4. Maleate, citraconate and 2,3-dimethylmaleate were rapidly hydrated by cell extracts, but ethylfumarate and 2,3-dimethylfumarate were not attacked. 5. Cell extracts oxidized 1,4-dihydroxy-2-naphthoate to give pyruvate and phthalate. 6. Alkylgentisates were oxidized by a gentisate oxygenase (EC 1.13.1.4) present in Pseudomonas 2,5. The ring-fission products were attacked by maleylpyruvase, but not by fumarylpyruvase, and their u.v.-absorption spectra were those expected for alkyl-substituted maleylpyruvates. 7. When supplemented with ATP, CoA, succinate and Mg(2+) ions, an enzyme system from cells grown with 2,5-xylenol formed pyruvate from d- but not from l-citramalate. Extracts from cells grown with dl-citramalate or with itaconate attacked both d- and l-citramalate; other alkylmalates were cleaved in similar fashion to give pyruvate or 2-oxobutyrate. 8. These results accord with a general sequence of reactions in which the benzene nucleus of an alkylgentisate is cleaved to give an alkyl-substituted maleylpyruvate. The ring-fission products are hydrolysed to give pyruvate, plus alkylmalic acids which then undergo aldol fissions, probably as their CoA esters. In Pseudomonas 2,5 several homologous sequences of this general type appear to be catalysed by a single battery of enzymes with broad substrate specificities, whereas the metabolic capabilities of the fluorescent Pseudomonas 3,5 are more restricted. 9. Intact cells of both organisms metabolize d-malic acid by reactions that have not been elucidated, but are different from those which degrade alkylmalates.

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“…[ 120 ] The earliest reports on anthracenes (Figure 4A‐a6) undergoing [4+4] photocycloaddition reactions date back to 1936. [ 129 ] Photocycloaddition occurs under λ > 300 nm UV exposure and scission of dimers occurs at λ < 300 nm or can be induced by heat. Compared with self‐healable cinnamates, anthracenes exhibit less strict requirements for tuning into specific UV wavelengths, and photo‐dimerization reactions are more efficient in a solid state.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Stimuli‐Responsive Commodity Polymers

Wang

Liu

et al. 2021

Macromol. Rapid Commun.

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Known for their adaptability to surroundings, capability of transport control of molecules, or the ability of converting one type of energy to another as a result of external or internal stimuli, responsive polymers play a significant role in advancing scientific discoveries that may lead to an array of diverge applications. This review outlines recent advances in the developments of selected commodity polymers equipped with stimuli‐responsiveness to temperature, pH, ionic strength, enzyme or glucose levels, carbon dioxide, water, redox agents, electromagnetic radiation, or electric and magnetic fields. Utilized diverse applications ranging from drug delivery to biosensing, dynamic structural components to color‐changing coatings, this review focuses on commodity acrylics, epoxies, esters, carbonates, urethanes, and siloxane‐based polymers containing responsive elements built into their architecture. In the context of stimuli‐responsive chemistries, current technological advances as well as a critical outline of future opportunities and applications are also tackled.

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The Structure of Anthracene

Cited by 20 publications

References 0 publications

Regioselective Claisen rearrangements in indoles

Regioselective Claisen rearrangements in indoles

The enzymic degradation of alkyl-substituted gentisates, maleates and malates

Recent Advances in Stimuli‐Responsive Commodity Polymers

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