Neighboring carboxyl group catalysis of hydrolysis of methyl phenyl acetals of formaldehyde. Electrostatic and solvent effects

1970 ◽  
Vol 92 (22) ◽  
pp. 6589-6594 ◽  
Author(s):  
Thomas C. Bruice ◽  
Ben M. Dunn
Keyword(s):  
Solvent Effects ◽  
Carboxyl Group ◽  
Hydrolysis Of ◽  
Methyl Phenyl

Improved synthesis of anti-sesquinorbornene

1984 ◽  
Vol 62 (9) ◽  
pp. 1840-1844 ◽  
Author(s):  
Karl R. Kopecky ◽  
Alan J. Miller
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Lead Tetraacetate ◽  
Carboxyl Group ◽  
Silver Acetate ◽  
Benzenesulfonyl Chloride ◽  
Methoxide Ion ◽  
Hydrolysis Of ◽  
Monomethyl Ester

Treatment of methyl hydrogen decahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a,8a-dicarboxylate with lead tetraacetate in benzene – acetic acid replaces the carboxyl group by an acetoxy group. Hydrolysis of this product with 25% sulfuric acid at 130 °C forms 8a-hydroxydecahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a-carboxylic acid 10. The reaction between 10 and benzenesulfonyl chloride in pyridine containing triethylamine at 95 °C produces anti-sesquinorbornene 1 in 34% yield. In the absence of triethylamine 1 is converted to the hydrochloride. The iodohydroperoxide of 1 is converted by silver acetate at 0 °C to the diketone in a luminescent reaction. The 1,2-dioxetane could not be isolated. Decahydro-1,4:5,8-exo,exo-dimethanonaphthalene-4a,8a-dicarboxylic anhydride is converted slowly by methoxide ion in methanol at 150 °C to the monomethyl ester which then undergoes demethylation. The isomeric exo,endo anhydride undergoes reaction readily with methoxide ion at 80 °C.

Solvent effects on the acid catalysed hydrolysis of benzamide, N-methylbenzamide, and NN-dimethylbenzamide

1972 ◽  
pp. 1869 ◽  
Author(s):  
C. A. Bunton ◽  
S. J. Farber ◽  
A. J. G. Milbank ◽  
Charmian J. O'Connor ◽  
T. A. Turney
Keyword(s):  
Solvent Effects ◽  
Hydrolysis Of

Reactivity of base catalysed hydrolysis of 2-pyridinylmethylene-8-quinolinyl-Schiff base iron(II) iodide complexes: solvent effects

2013 ◽  
Vol 67 (4) ◽  
Author(s):  
Ahmad Mohamad ◽  
Mohamed Adam
Keyword(s):  
Aqueous Solution ◽  
Schiff Base ◽  
Solvent Effects ◽  
Base Hydrolysis ◽  
Iodide Ions ◽  
Ligand Structure ◽  
Solvation Parameters ◽  
Kinetics Of ◽  
Hydrolysis Of ◽  
Direct Condensation

AbstractThree ligands of 2-pyridinylmethylene-8-quinolinyl (L1), methyl-2-pyridinylmethylene-8-quinolinyl (L2), and phenyl-2-pyridinylmethylene-8-quinolinyl (L3), Schiff bases were synthesised by direct condensation of 8-aminoquinoline with 2-pyridinecarboxaldehyde, 2-acetylpyridine, or 2-benzoylpyridine. They coordinated to Fe(II) ion in a 1: 2 mole ratio followed by treatment with iodide ions affording complexes with a general formula [Fe(L)2]I2·2H2O, (L = L1, L2, or L3). Spectrophotometric evaluation of the kinetics of base catalysed hydrolysis of these complex cations was carried out with an aqueous solution of NaOH in different ratios of water/methanol binary mixtures. Kinetics of the hydrolysis followed the rate law (k 2[OH−] + k 3[OH−]2)[complex]. Reactivity trends and their rate constants were compared and discussed in terms of ligand structure and solvation parameters. The methanol ratio affects the hydrolysis as a co-solvent which was analysed into initial and transition state components. The increase in the rate constant of the base hydrolysis of Fe(II) complexes, as the ratio of methanol increases, is predominantly caused by the strong effect of the organic co-solvent on the transition states.

Copper catalysed hydrolysis of acrylonitrile to acrylamide: Solvent effects

1990 ◽  
Vol 57 (1) ◽  
pp. 215-222 ◽  
Author(s):  
J.C. Lee ◽  
N.W. Cant ◽  
D.L. Trimm ◽  
M.S. Wainwright
Keyword(s):  
Solvent Effects ◽  
Hydrolysis Of
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