Efficient and Green Telescoped Process to 2-Methoxy-3-methyl-[1,4]benzoquinone

González, R.; Gambarotti, Cristian; Liguori, Lucia; Bjørsvik, Hans‐René

doi:10.1021/jo0522512

Cited by 22 publications

(26 citation statements)

References 28 publications

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“…S14-S18). These NMR data corresponded well with the literature (Gonzáles et al, 2006;Miyamura et al, 2008), with the exception of the coupling between the -CH 3 group and H-3 of compound II. We observed this coupling in the 1 H NMR spectrum (Fig.…”

Section: Resultssupporting

confidence: 89%

Composition of the Defensive Secretion in Three Species of European Millipedes

et al. 2011

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Three European julid species, Cylindroiulus boleti, Leptoiulus trilineatus, and Megaphyllum bosniense, secrete mixtures of up to 12 different quinones. The major components in these species are 2-methoxy-3-methyl-1,4-benzoquinone and 2-methyl-1,4-benzoquinone. 2-Methoxy-5-methylhydroquinone is detected for the first time in the Class Diplopoda. 2-Hydroxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxyhydroquinone, 2-methyl-3,4-methylendioxyphenol, and 2,3-dimethoxy-5-methylhydroquinone are registered for the first time in representatives of the family Julidae. The similar chemical composition of defense secretions in all analyzed European julids and Pacific spirobolids supports the idea of the chemical consistency of defensive compounds in juliform millipedes.

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Section: Resultssupporting

confidence: 89%

Composition of the Defensive Secretion in Three Species of European Millipedes

et al. 2011

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“…187 The compound 141 is produced selectively in high yield (95%) by a single pot telescoped oxidation process composed of three partial steps: …”

Section: Synthesis Of Benzoquinones From Dimethoxybenzenesmentioning

confidence: 99%

“…Recently Atalar et al 214 extended the investigation on pentalenoquinones (PQs) to bromopentalenoquinones (185)(186)(187)(188)(189) to reveal the stability and aromatic character. Baik et al 215 accomplished the reactivity and stability studies of benzoquinones methides by ab initio calculations.…”

Section: Computational Investigations On 14-benzoquinonesmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

169

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As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

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“…Acetylation of 1,4-dimethoxybenzene with acetic anhydride/phosphoric acid gave 2-acetyl-1,4-dimethoxybenzene. Subsequent Bayer-Villiger oxidation with p-toluenesulfonic acid/hydrogen peroxide in acetic acid [46] gave 2,5-dimethoxyphenyl acetate in 97 % yield. Subsequent Bayer-Villiger oxidation with p-toluenesulfonic acid/hydrogen peroxide in acetic acid [46] gave 2,5-dimethoxyphenyl acetate in 97 % yield.…”

Section: Resultsmentioning

confidence: 99%

“…1 2,5-Dimethoxyphenol (9): [46] Water (40 mL) was added to 2,5-dimethoxyphenyl acetate [46] (5.95 g, 30.4 mmol) in ethanol (60 mL), and the mixture was heated to 70°C. Reaction vessels were heated at reduced pressure with a heat gun and flushed with nitrogen.…”

Section: Methodsmentioning

confidence: 99%

Attempts Directed towards the Synthesis of Intermediate (Aryne)chromium Complexes from Aryl Triflates and from (Haloarene)chromium Complexes

Werner

Butenschön

2012

Eur J Org Chem

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The generation of (η6‐aryne)chromium complexes as reactive intermediates was investigated in two ways. Although earlier attempts directed towards triflate eliminations from a variety of tricarbonyl(phenyl triflate)chromium complexes had failed, more electron‐rich phenyl triflate complexes were considered. This was accomplished either by substitution with two methoxy groups in the arene ligand or by replacement of one of the three carbonyl ligands of the tricarbonylchromium complex with triphenylphosphane. However, the attempted elimination still did not take place; in spite of the increased electron densities in the aromatic ligands, anionic thia‐Fries rearrangements were observed in high yields at –78 °C. As an alternative, elimination of lithium fluoride was tested. Tricarbonyl(2‐lithiofluorobenzene)chromium(0) was generated by tin/lithium exchange. After hydrolytic workup, tricarbonyl(fluorobenzene)chromium was obtained as the main product, indicating that the lithiation step had been successful. A dimeric side product provided evidence for the intermediacy of (benzyne)tricarbonylchromium.

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Efficient and Green Telescoped Process to 2-Methoxy-3-methyl-[1,4]benzoquinone

Cited by 22 publications

References 28 publications

Composition of the Defensive Secretion in Three Species of European Millipedes

Composition of the Defensive Secretion in Three Species of European Millipedes

Recent advances in 1,4-benzoquinone chemistry

Attempts Directed towards the Synthesis of Intermediate (Aryne)chromium Complexes from Aryl Triflates and from (Haloarene)chromium Complexes

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