Ortho ester hydrolysis: concerted nature of the dialkoxycarbonium ion forming stage

1979 ◽  
Vol 44 (10) ◽  
pp. 1639-1642 ◽  
Author(s):  
R. G. Bergstrom ◽  
M. J. Cashen ◽  
Y. Chiang ◽  
A. J. Kresge
Keyword(s):  
Ester Hydrolysis ◽  
Ortho Ester

Ortho ester hydrolysis: direct evidence for a three-stage reaction mechanism

1979 ◽  
Vol 101 (10) ◽  
pp. 2669-2677 ◽  
Author(s):  
M. Ahmad ◽  
R. G. Bergstrom ◽  
M. J. Cashen ◽  
Y. Chiang ◽  
A. J. Kresge ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Direct Evidence ◽  
Ester Hydrolysis ◽  
Ortho Ester

Ortho Ester Hydrolysis: Direct Evidence for a Three-Stage Reaction Mechanism - Correction

1982 ◽  
Vol 104 (4) ◽  
pp. 1156-1157 ◽  
Author(s):  
M Ahmad ◽  
R Bergstrom ◽  
M Cashen ◽  
Y Chiang ◽  
A Kresge ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Direct Evidence ◽  
Ester Hydrolysis ◽  
Ortho Ester

Carbonyl oxygen exchange of glycol monoesters. Rate and equilibrium constants for the formation of a tetrahedral intermediate

1979 ◽  
Vol 57 (12) ◽  
pp. 1531-1540 ◽  
Author(s):  
R. A. McClelland ◽  
M. Ahmad ◽  
J. Bohonek ◽  
S. Gedge
Keyword(s):  
Equilibrium Constant ◽  
Rate Constants ◽  
Equilibrium Constants ◽  
Carbonyl Oxygen ◽  
Ester Hydrolysis ◽  
Oxygen Exchange ◽  
Ortho Ester ◽  
Kinetic Investigations ◽  
Relationship Of ◽  
The Relationship

Kinetic investigations of the hydrolysis of the 2-phenyl-4,4,5,5-tetramethyl-1,3-dioxolenium ion and 2-phenyl-2-methoxy-4,4,5,5-tetramethyl-1,3-dioxolane furnish rate constants for all three reaction stages of the ortho ester hydrolysis: (1) generation of the dioxolenium ion, (2) hydration of this ion to form hydrogen ortho ester, and (3) breakdown of this species to pinacol monobenzoate. The equilibrium constant for stage (2) can also be obtained. This study complements a previous investigation of 2-phenyl-2-alkoxy-1,3-dioxolanes where similar information was obtained.The rate constants for carbonyl oxygen exchange of the ester products of these reactions, pinacol monobenzoate and ethylene glycol monobenzoate, have been measured. This reaction is shown to proceed by a different mechanism to that normally associated with exchange of carboxylic acid derivatives: cyclization of the glycol monoester to form hydrogen ortho ester, followed by loss of the labelled exocyclic OH group to give 1,3-dioxolenium ion. Reversal of these steps, initiated by an unlabelled water molecule, results in exchange. The relationship of this mechanism with that of the ortho ester hydrolysis is obvious; it is shown that the exchange provides rate constants for the reverse of stage (3). This means that both the forward and reverse rates of this process have been obtained, and this provides the equilibrium constant.

ChemInform Abstract: EFFECT OF PHENYL SUBSTITUTION ON ORTHO ESTER HYDROLYSIS

1974 ◽  
Vol 5 (38) ◽  
pp. no-no
Author(s):  
Y. CHIANG ◽  
A. J. KRESGE ◽  
P. SALOMAA ◽  
C. I. YOUNG
Keyword(s):  
Ester Hydrolysis ◽  
Ortho Ester

ChemInform Abstract: ORTHO ESTER HYDROLYSIS. THE COMPLETE REACTION MECHANISM

1977 ◽  
Vol 8 (41) ◽  
pp. no-no
Author(s):  
M. AHMAD ◽  
R. G. BERGSTROM ◽  
M. J. CASHEN ◽  
A. J. KRESGE ◽  
R. A. MCCLELLAND ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Ester Hydrolysis ◽  
Ortho Ester ◽  
Complete Reaction

ChemInform Abstract: ORTHO ESTER HYDROLYSIS: CONCERTED NATURE OF THE DIALKOXYCARBONIUM ION FORMING STAGE

1979 ◽  
Vol 10 (37) ◽  
Author(s):  
R. G. BERGSTROM ◽  
M. J. CASHEN ◽  
Y. CHIANG ◽  
A. J. KRESGE
Keyword(s):  
Ester Hydrolysis ◽  
Ortho Ester

Ortho ester hydrolysis. The complete reaction mechanism

1977 ◽  
Vol 99 (14) ◽  
pp. 4827-4829 ◽  
Author(s):  
M. Ahmad ◽  
R. G. Bergstrom ◽  
M. J. Cashen ◽  
A. J. Kresge ◽  
R. A. McClelland ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Ester Hydrolysis ◽  
Ortho Ester ◽  
Complete Reaction

Effect of phenyl substitution on ortho ester hydrolysis

1974 ◽  
Vol 96 (14) ◽  
pp. 4494-4499 ◽  
Author(s):  
Y. Chiang ◽  
A. J. Kresge ◽  
P. Salomaa ◽  
C. I. Young
Keyword(s):  
Ester Hydrolysis ◽  
Ortho Ester

General acid catalysis of ortho ester hydrolysis

1972 ◽  
Vol 37 (12) ◽  
pp. 1993-1996 ◽  
Author(s):  
Edwin. Anderson ◽  
Thomas H. Fife
Keyword(s):  
Acid Catalysis ◽  
Ester Hydrolysis ◽  
Ortho Ester ◽  
General Acid

ChemInform Abstract: ORTHO ESTER HYDROLYSIS: DIRECT EVIDENCE FOR A THREE-STAGE REACTION MECHANISM

1979 ◽  
Vol 10 (34) ◽  
Author(s):  
M. AHMAD ◽  
R. G. BERGSTROM ◽  
M. J. CASHEN ◽  
Y. CHIANG ◽  
A. J. KRESGE ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Direct Evidence ◽  
Ester Hydrolysis ◽  
Ortho Ester
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