<b>Decomposition Reactions of Alkyl Chloroglyoxalates</b>

Rhoads, Sara Jane; Michel, Robert E.

doi:10.1021/ja00888a023

Cited by 40 publications

(16 citation statements)

References 3 publications

(6 reference statements)

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“…This is a major drawback of this method. 5 Hence, the double carbonylation methodology provides an efficient alternative for the synthesis of these industrially valuable products.…”

Section: Introductionmentioning

confidence: 99%

Recent developments in palladium catalysed carbonylation reactions

2014

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“…This is a major drawback of this method. 5 Hence, the double carbonylation methodology provides an efficient alternative for the synthesis of these industrially valuable products.…”

Section: Introductionmentioning

confidence: 99%

Recent developments in palladium catalysed carbonylation reactions

2014

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“…Alkyne‐PO‐SS‐PO‐alkyne was synthesized in two steps according to the reported procedure with minor modification. [ 26,27 ] First, oxalyl chloride (18.00 mL, 209.76 mmol) was dissolved in 60 mL anhydrous DCM in a dried 250 mL round bottom flask and stirred for 10 min in an ice bath. Then 20 mL anhydrous DCM containing propargyl alcohol (5.0 g, 89.29 mmol) was slowly dropped into the reaction within 30 min.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Photo, Oxidation, Reduction Triple‐Stimuli‐Responsive Interface‐Cross‐Linked Polymer Micelles as Nanocarriers for Controlled Release

Guo

Liu

Yang

et al. 2021

Macro Chemistry & Physics

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Stimuli‐responsive chemical bonds have already been widely applied to construct nanomaterials, however, such materials rarely have great amounts of responsive groups and stable structures. Herein, a triple‐stimuli‐responsive interface‐cross‐linked (ICL) copolymer which is synthesized via Cu(I)‐catalyzed azide‐alkyne cycloaddition click polymerization and atom transfer radical polymerization (ATRP), is reported. N, N′‐bis(bromoacetyl) cystamine is used for intramolecular crosslinking of the linear polymer chains. The ο‐nitrobenzyl groups, peroxalate ester bonds, disulfide bonds, and triazole units are regularly and repeatedly arranged in the hydrophobic blocks, therefore enabling the polymer a large amount of responsive chemical bonds. The polymer self‐assembles into spherical micelles with uniform size in deionized water. Using hydrophobic dye Nile red (NR) as a model drug to evaluate the effect of release in vitro, the multi‐stimuli‐sensitive release properties of the ICL micelles are investigated in detail by means of UV–vis, transmission electron microscopy, dynamic light scattering, and fluorescence spectrophotometry, and the results indicate the ICL micelles can respond to the photo, oxidation, or reduction responsiveness either independently or synergistically. Furthermore, the cross‐linked structure enhances the stability of the micelles and rarely impacts the total amount of drug release. The research may have applications in the field of drug delivery systems for cancer therapy.

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“…2,6-Bis(pent-4-enyloxy)-aniline [22] (10a), 2,6-bis(hex-5-enyloxy)aniline [22] (10b), 2,7-dihydroxy-1-nitronaphthalene [58] (7), and ethyl chloroglyoxalate [59] were synthesized according to literature procedures. Tetrahydrofuran was dried by heating at reflux with lithium aluminum hydride.…”

Section: Methodsmentioning

confidence: 99%

“…General Remarks: The following chemicals were obtained commercially and used without further purification: benzylidene-bis(tricyclohexylphosphane)dichlororuthenium (Aldrich), diisopropylazodicarboxylate (Fluka), 2,7-dihydroxynaphthalene (Fluka), dimethyl sulfate (Acros), 5-hexen-1-ol (Merck), lithium aluminum hydride (Merck), 2-nitroresorcinol (Alfa Aesar), oxalyl chloride (Fluka), palladium/charcoal (10 % Pd, Merck), 4-penten-1-ol (Alfa Aesar), stannous chloride dihydrate (Fluka), triethyl orthoformate (Merck), and triphenylphosphane (Fluka). 2,6-Bis(pent-4-enyloxy)aniline [22] (10a), 2,6-bis(hex-5-enyloxy)aniline [22] (10b), 2,7-dihydroxy-1-nitronaphthalene [58] (7), and ethyl chloroglyoxalate [59] were synthesized according to literature procedures. Tetrahydrofuran was dried by heating at reflux with lithium aluminum hydride.…”

Section: Methodsmentioning

confidence: 99%

Chiral Concave Imidazolinium Salts as Precursors to Chiral Concave N‐Heterocyclic Carbenes

et al. 2007

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Imidazolinium moieties have been incorporated into bimacrocycles to generate precursors for concave N‐heterocyclic carbenes (NHCs). By using one symmetrically substituted benzene bridgehead and one naphthalene bridgehead devoid of local C2‐symmetry, axially chiral concave imidazolinium ions have been obtained. Starting from 2,7‐dihydroxy‐1‐nitronaphthalene (7), the phenol groups have been transformed to 4‐pentenyl ethers 8, and the nitro group was then reduced to the corresponding amine 9. Next, 9 and a 2,6‐bis(alkenyloxy)aniline 10 were connected by an oxalic acid linker. After reduction of the diamide 13 to diamine 14, a bridge was installed with triethyl orthoformate to give a tetraalkenyl‐substituted imidazolinium salt 15. Ring‐closing metathesis of 15 followed by hydrogenation of the products 16 yielded the bimacrocyclic salts 17 in 9–18 % overall yield (based on 7), giving amounts up to >300 mg. The configurational stability of 17 was investigated by NMR using chiral enantiopure anions TRISPHAT 18 and BINPHAT 19 as stereodynamic probes.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Decomposition Reactions of Alkyl Chloroglyoxalates

Cited by 40 publications

References 3 publications

Recent developments in palladium catalysed carbonylation reactions

Recent developments in palladium catalysed carbonylation reactions

Synthesis of Photo, Oxidation, Reduction Triple‐Stimuli‐Responsive Interface‐Cross‐Linked Polymer Micelles as Nanocarriers for Controlled Release

Chiral Concave Imidazolinium Salts as Precursors to Chiral Concave N‐Heterocyclic Carbenes

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