Hydrolysis of the vinyl ether functional group in a model for prostacyclin in which the carboxyl group has been replaced by a pyridine ring

1989 ◽  
Vol 54 (9) ◽  
pp. 2137-2142 ◽  
Author(s):  
Nils Aake Bergman ◽  
Torbjoern Halvarsson
Keyword(s):  
Vinyl Ether ◽  
Pyridine Ring ◽  
Functional Group ◽  
Carboxyl Group ◽  
Hydrolysis Of

scholarly journals Vinyl ether hydrolysis. XIV. 2-Methoxy-2,3-dihydropyran: concurrent reaction of vinyl ether and acetal functional groups

1980 ◽  
Vol 58 (21) ◽  
pp. 2199-2202 ◽  
Author(s):  
R. A. Burt ◽  
Y. Chiang ◽  
A. J. Kresge
Keyword(s):  
Vinyl Ether ◽  
Isotope Effect ◽  
Reaction Rate ◽  
Functional Group ◽  
Minor Amount ◽  
Cyanoacetic Acid ◽  
Buffer Solutions ◽  
Hydrogen Isotope Effect ◽  
A Minor ◽  
Hydrolysis Of

The hydrolysis of 2-methoxy-2,3-dihydropyran shows a normal isotope effect (kH/kD > 1) under catalysis by the hydrogen ion and gives an accurately linear dependence of reaction rate upon undissociated acid concentration in cyanoacetic acid and formic acid buffer solutions. This substrate, therefore, unlike its higher homolog, 9-methoxyoxacyclonon-2-ene, provides no evidence in support of an anything but a normal mechanism for vinyl ether hydrolysis. Analysis of the hydrogen isotope effect suggests that a minor amount (8%) of this hydrolysis occurs via reaction of the acetal functional group.

ChemInform Abstract: Acid-Catalyzed Hydrolysis of Vinyl Acetals. Reaction Through the Acetal Rather Than the Vinyl Ether Functional Group.

ChemInform ◽  
1989 ◽  
Vol 20 (49) ◽  
Author(s):  
Y. CHIANG ◽  
W. K. CHWANG ◽  
A. J. KRESGE ◽  
Y. YIN
Keyword(s):  
Vinyl Ether ◽  
Functional Group ◽  
Acid Catalyzed ◽  
Vinyl Acetals ◽  
Hydrolysis Of

Acid-catalyzed hydrolysis of vinyl acetals. Reaction through the acetal rather than the vinyl ether functional group

1989 ◽  
Vol 111 (18) ◽  
pp. 7185-7190 ◽  
Author(s):  
Y. Chiang ◽  
W. K. Chwang ◽  
A. J. Kresge ◽  
Y. Yin
Keyword(s):  
Vinyl Ether ◽  
Functional Group ◽  
Acid Catalyzed ◽  
Vinyl Acetals ◽  
Hydrolysis Of

Kinetics of hydrolysis of vinyl ether functional group of the stable, bioactive prostacyclin analog taprostene (CG 4203)

1988 ◽  
Vol 53 (11) ◽  
pp. 2552-2555 ◽  
Author(s):  
Y. Chiang ◽  
A. J. Kresge ◽  
U. Seipp ◽  
W. Winter
Keyword(s):  
Vinyl Ether ◽  
Functional Group ◽  
Kinetics Of Hydrolysis ◽  
Kinetics Of ◽  
Hydrolysis Of ◽  
Prostacyclin Analog

Acid-catalyzed hydrolysis of 5-enolpyruvylshikimate 3-phosphate (EPSP) and some simple models of its vinyl ether functional group

1992 ◽  
Vol 114 (7) ◽  
pp. 2618-2622 ◽  
Author(s):  
A. Jerry Kresge ◽  
Mordechai Leibovitch ◽  
James A. Sikorski
Keyword(s):  
Vinyl Ether ◽  
Functional Group ◽  
Acid Catalyzed ◽  
Hydrolysis Of ◽  
Simple Models

ChemInform Abstract: Kinetics of Hydrolysis of the Vinyl Ether Functional Group of the Stable, Bioactive Prostacyclin Analogue Taprostene (CG 4203).

ChemInform ◽  
1988 ◽  
Vol 19 (42) ◽  
Author(s):  
Y. CHIANG ◽  
A. J. KRESGE ◽  
U. SEIPP ◽  
W. WINTER
Keyword(s):  
Vinyl Ether ◽  
Functional Group ◽  
Prostacyclin Analogue ◽  
Kinetics Of Hydrolysis ◽  
Kinetics Of ◽  
Hydrolysis Of

scholarly journals Isothermal and non-isothermal kinetics of hydrolysis of 1-[2-(2- pentyloxyphenylcarbamoyloxy)-(2-methoxymethyl)-ethyl]- perhydroazepinium chloride (BK 129)

2013 ◽  
Vol 60 (2) ◽  
pp. 43-48
Author(s):  
Stankovičová M. ◽  
Bezáková Ž. ◽  
Beňo P. ◽  
Húšťavová P.
Keyword(s):  
Biological Activity ◽  
Alkaline Hydrolysis ◽  
Functional Group ◽  
Isothermal Kinetics ◽  
Basic Part ◽  
Buffer Solutions ◽  
Kinetics Of Hydrolysis ◽  
Short Time ◽  
Kinetics Of ◽  
Hydrolysis Of

Abstract The substance BK 129 - 1-[2-(2-pentyloxyphenylcarbamoyloxy)-(2-methoxymethyl)-ethyl]-perhydroazepinium chloride was prepared in terms of influence of the connecting chain between the carbamate functional group and the basic part of molecule on biological activity. Such a structural feature is important with regard to its stability. In this work we determined the rate constants of alkaline hydrolysis of this compound at increased temperature under isothermal and non-isothermal conditions. The hydrolysis was also performed in buffer solutions with the purpose of evaluating its stability. Non-isothermal tests of stability enable to reduce the number of analyses. The necessary data for stability of compound are in this way achieved in a short time.

Vinyl ether hydrolysis. XVII. Oxacyclonon-2,8-diene and the question of the unorthodox reaction mechanism for 9-methoxyoxacyclonon-2-ene

1984 ◽  
Vol 62 (1) ◽  
pp. 74-76 ◽  
Author(s):  
R. A. Burt ◽  
Y. Chiang ◽  
A. J. Kresge ◽  
S. Szilagyi
Keyword(s):  
Reaction Mechanism ◽  
Vinyl Ether ◽  
Membered Ring ◽  
Specific Rate ◽  
Ether Group ◽  
Reaction Proceeds ◽  
Great Reactivity ◽  
Rate Of Hydrolysis ◽  
Acid Catalyzed ◽  
Hydrolysis Of

The acid-catalyzed hydrolysis of the nine-membered ring cyclic vinyl ether, oxacyclonon-2,8-diene, occurs with a normal isotope effect, [Formula: see text], which indicates that this reaction proceeds by the conventional vinyl ether hydrolysis mechanism involving rate-determining proton transfer to carbon. The specific rate of this reaction, [Formula: see text], may then be used to show that there is no significant ring-size effect on the rate of hydrolysis of a vinyl ether group in a nine-membered ring. The previously noted unusually great reactivity of the vinyl ether group in 9-methoxyoxacyclonon-2-ene, for which an unorthodox reaction mechanism has been claimed, must therefore be due to some other cause.

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