Ringöffnung bei Benz‐α, β‐isoxazolen

Lindemann, Hans; Cisséc, Hans

doi:10.1002/jlac.19294690106

Cited by 25 publications

(9 citation statements)

References 3 publications

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“…The substrate 6-nitro-5-methyl-benzisoxazole-3-carboxylic acid was prepared from methyl 3-methylphenyl acetate by the general method used for the parent compound [24]. Nitration (KNO 3 /H 2 SO 4 ) gave the 4,6-dinitro derivative, which was cyclized to methyl 6-nitro-5-methylbenzisoxazole-3-carboxylate, m.p.…”

Section: Methodsmentioning

confidence: 99%

Temperature effects upon aqueous micellar-assisted decarboxylation of 6-nitrobenzisoxazole-3-carboxylate and its 5-methyl derivative

Brinchi

Germani

Goracci

et al. 2006

Journal of Colloid and Interface Science

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Section: Methodsmentioning

confidence: 99%

Temperature effects upon aqueous micellar-assisted decarboxylation of 6-nitrobenzisoxazole-3-carboxylate and its 5-methyl derivative

Brinchi

Germani

Goracci

et al. 2006

Journal of Colloid and Interface Science

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“…Kinetic Measurements. 6-Nitrobenzisoxazole-3-carboxylate ( 1 ; 6-NBIC) was prepared according to a literature procedure. , First-order rate constants for the decarboxylation of 1 were measured at 30.0 ± 0.1 °C by monitoring the increase in absorption at 410 nm for at least 4 half-lives, using a Perkin Elmer λ5 or Perkin Elmer λ2 spectrophotometer. The rate constants ( k obs , reproducible to within 3%) were calculated using the Guggenheim method for the PE λ5 and Enzfitter (a fitting program) for the PE λ2.…”

Section: Methodsmentioning

confidence: 99%

Self-Assembly in Mixtures of Sodium Alkyl Sulfates and Alkyltrimethylammonium Bromides: Aggregation Behavior and Catalytic Properties

Talhout

Engberts

1997

Langmuir

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Two aqueous mixtures of cationic and anionic surfactants have been studied by means of conductometry, transmission electron microscopy, and microcalorimetry. Their catalytic effects on the decarboxylation of the kinetic probe 6-nitrobenzisoxazole-3-carboxylate (6-NBIC) were also examined in some detail. The mixtures differ profoundly in the hydrophobic match between both surfactant tails, which is perfect for dodecyltrimethylammonium bromide (DTAB) and sodium dodecyl sulfate (SDS) and poor for hexadecyltrimethylammonium bromide (CTAB) and sodium heptyl sulfate (SHS). This difference is reflected in the more pronounced synergism in critical aggregation concentration and catalytic efficiency of the DTAB/SDS mixture and in the phase behavior of the mixtures. CTAB and SHS can be mixed in a 1:1 ratio without precipitation, forming both small, unilamellar and large, multilamellar vesicles. In DTAB/SDS mixtures, however, precipitation of the catanionic surfactant occurs for a mole fraction of DTAB (x) between 0.3 and 0.7, while both vesicles and large bilayer fragments are formed for x = 0.8. The excess of DTAB in the x = 0.8 mixture results in the solubilization of the vesicles by DTAB micelles close to the cmc of pure DTAB. A network of interconnected threadlike cylindrical micelles was found as an intermediate stage of aggregation between the vesicles and the mixed micelles. These cylindrical micelles are formed exclusively on further increasing the surfactant concentration.

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“…All chemicals were used without further purification. 6-Nitrobenzisoxazole-3-carboxylate (6-NBIC) was synthesized according to a literature procedure 10,11 and was stored at À208C.…”

Section: Methodsmentioning

confidence: 99%

Vesicular catalysis of the decarboxylation of 6‐nitrobenzisoxazole‐3‐carboxylate. The effects of sugars, long‐tailed sugars, cholesterol and alcohol additives

Jongejan

Klijn

Engberts

et al. 2006

J of Physical Organic Chem

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Vesicular catalysis of the decarboxylation of 6-nitrobenzisoxazole-3-carboxylate. The effects of sugars, long-tailed sugars, cholesterol and alcohol additives Jongejan, Mahthild G. M.; Klijn, Jaap E.; Engberts, Jan. B. F. N.; Kiijn, J.E. Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. ABSTRACT: The effects of the addition of sugars, long-tailed n-alkyl pyranosides, n-alkyl glycerol ethers and nalcohols on the properties of di-n-hexadecyldimethylammonium bromide (DHAB) vesicles have been studied. Properties that were examined include the stability, morphology, phase of the tails, and catalytic rate acceleration of the unimolecular decarboxylation of the 6-nitrobenzisoxazole-3-carboxylate anion (6-NBIC). The kinetic data were analyzed on the basis of the pseudophase model and show a rate acceleration of a factor of about 1000 relative to the reaction in water. Upon addition of most additives an inhibiting effect on the decarboxylation reaction of 6-NBIC is observed relative to the reaction in vesicles without any additive. The largest inhibition was observed in the case of cholesterol. Contrastingly, n-dodecyl-b-maltoside (in the spherical vesicle region) and trehalose accelerate the reaction. The activation parameters show that the most significant contribution to the Gibbs energy of activation is the enthalpic factor, with a partly compensating entropic contribution.

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Ringöffnung bei Benz‐α, β‐isoxazolen

Cited by 25 publications

References 3 publications

Temperature effects upon aqueous micellar-assisted decarboxylation of 6-nitrobenzisoxazole-3-carboxylate and its 5-methyl derivative

Temperature effects upon aqueous micellar-assisted decarboxylation of 6-nitrobenzisoxazole-3-carboxylate and its 5-methyl derivative

Self-Assembly in Mixtures of Sodium Alkyl Sulfates and Alkyltrimethylammonium Bromides: Aggregation Behavior and Catalytic Properties

Vesicular catalysis of the decarboxylation of 6‐nitrobenzisoxazole‐3‐carboxylate. The effects of sugars, long‐tailed sugars, cholesterol and alcohol additives

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