Zur Reaktion von Carbons�ureanhydriden mit Formamid und N-Methylformamid

Schindlbauer, H.

doi:10.1007/bf00910596

Cited by 15 publications

(6 citation statements)

References 6 publications

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“…Continuous separation was performed using a 500‐mL Normag TM liquid‐liquid extractor (for solvents lighter than water). All products are known and have been described previously 27–30.…”

Section: Methodsmentioning

confidence: 99%

Photodecarboxylations in an Advanced Meso‐Scale Continuous‐Flow Photoreactor

2015

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Selected photodecarboxylations of phthalimides were realized under continuousflow conditions using an advanced meso-scale photoreactor. The improved efficiency, yields, and productivities of these photochemical reactions highlight the benefits of using flow as opposed to conventional batch operation modes. Flow chemistry furthermore allows for an easy combination of multiple reaction steps in series. This is demonstrated by the successful synthesis of a pharmaceutical target molecule through a tandem photochemical-thermal procedure carried out in uninterrupted flow.

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Section: Methodsmentioning

confidence: 99%

Photodecarboxylations in an Advanced Meso‐Scale Continuous‐Flow Photoreactor

2015

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“…Materials. 2-Methylisoindoline-1,3-dione ( 1 ) and 5,6-dimethoxy-2-methylisoindoline-1,3-dione ( 8 ) were prepared by the reaction of the respective phthalic anhydrides with N -methylformamide . 2-Isobutylisoindoline-1,3-dione ( 2 ) and 2-allylisoindoline-1,3-dione ( 3 ) were prepared by heating equimolar amounts of phthalic anhydride with the respective amines in the presence of small amounts of N , N -dimethylformamide.…”

Section: Methodsmentioning

confidence: 99%

Photoinduced Decarboxylative Benzylation of Phthalimide Triplets with Phenyl Acetates: a Mechanistic Study

2006

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The photodecarboxylative benzylation of N-alkyl, N-arylalkyl, and N-aryl phthalimides with arylacetic acids in aqueous solution proceeds via electron transfer from the arylalkanoate to the excited triplet state of the phthalimide, either formed directly or upon sensitization with acetone. The rate constant for triplet quenching of N-methylphthalimide is k(q) < 10(7) M(-1) s(-1) for 2-phenylacetic acid and k(q) = (1-3) x 10(9) M(-1) s(-1) for its mono-, di- and trimethoxy-substituted derivatives, suggesting a change of the mechanism for the primary oxidation step from a Photo-Kolbe type reaction yielding an acyloxy radical to a pseudo-Photo-Kolbe process involving the formation of resonance-stabilized zwitterion radicals as intermediates.

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“…Materials N-Methylated 4,5-dimethoxyphthalimide 1 was prepared from dimethoxyphthalic anhydride and N-methylformamide. 16 The functionalized 4,5-dimethoxyphthalimides 2-10 (Fig. 1) were prepared analogous to a literature procedure from dimethoxyphthalic anhydride and the corresponding amines.…”

Section: Methodsmentioning

confidence: 99%

Intra- and intermolecular fluorescence quenching of N-activated 4,5-dimethoxyphthalimides by sulfides, amines, and alkyl carboxylates

Griesbeck

Schieffer

2003

Photochem Photobiol Sci

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The fluorescent 4,5-dimethoxyphthalimides 1-10 were applied as sensors for intra- and intermolecular photoinduced electron transfer processes. Strong intramolecular fluorescence quenching was detected for the thioether 2 and the tertiary amine 3. The fluorescence of the carboxylic acids 4-7 is pH-dependent accounting for PET-quenching of the singlet excited phthalimide at pH > pKs. At low pH, chromophore protonation might contribute to moderate fluorescence quenching. The arylated phthalimides 9 and 10 show remarkable low fluorescence independent of pH and substituent pattern. Intermolecular fluorescence quenching was detected for the combinations of 1 with dimethyl sulfide, and 1 with triethylamine but not with metal carboxylates.

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Zur Reaktion von Carbons�ureanhydriden mit Formamid und N-Methylformamid

Cited by 15 publications

References 6 publications

Photodecarboxylations in an Advanced Meso‐Scale Continuous‐Flow Photoreactor

Photodecarboxylations in an Advanced Meso‐Scale Continuous‐Flow Photoreactor

Photoinduced Decarboxylative Benzylation of Phthalimide Triplets with Phenyl Acetates: a Mechanistic Study

Intra- and intermolecular fluorescence quenching of N-activated 4,5-dimethoxyphthalimides by sulfides, amines, and alkyl carboxylates

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