Kinetics and Mechanism of the Pinacol Rearrangement. I. The Perchloric Acid-catalyzed Rearrangement of Benzopinacol and of Tetraphenylethylene Oxide in Acetic Acid Solution1

1954 ◽  
Vol 76 (15) ◽  
pp. 3925-3930 ◽  
Author(s):  
Herbert J. Gebhart ◽  
Kenneth H. Adams
Keyword(s):  
Acetic Acid ◽  
Perchloric Acid ◽  
Kinetics And Mechanism ◽  
Pinacol Rearrangement ◽  
Acid Catalyzed

scholarly journals Acid-Catalyzed Hydrolysis of Some Secondary Alkyl Phenyl Ethers in Perchloric Acid: Kinetics and Mechanism.

1992 ◽  
Vol 46 ◽  
pp. 726-731 ◽  
Author(s):  
Martti Lajunen ◽  
Mika Kähkönen ◽  
Yngve Stenstrøm ◽  
Adolf Gogoll ◽  
Kjell Undheim ◽  
...  
Keyword(s):  
Perchloric Acid ◽  
Kinetics And Mechanism ◽  
Acid Catalyzed ◽  
Phenyl Ethers ◽  
Hydrolysis Of

SUBSTITUTION OF ACYCLIC SUGAR ACETALS: RATE OF PERCHLORIC ACID CATALYZED ACETOLYSIS OF 2,3,4,5,6-PENTA-O-ACETYL-D-GLUCOSE DIETHYL DITHIOACETAL AND 1,2,3,4,5,6-HEXA-O-ACETYL-D-GLUCOSE S-ETHYL MONOTHIOACETAL

1966 ◽  
Vol 44 (15) ◽  
pp. 1773-1782 ◽  
Author(s):  
Norman H. Kurihara ◽  
Edgar Page Painter
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Perchloric Acid ◽  
Rate Constants ◽  
Acetoxy Group ◽  
Rate Determining Step ◽  
Conjugate Acid ◽  
Acid Catalyzed ◽  
Sugar Derivatives

The rate constants for the perchloric acid catalyzed substitution of one ethylthio group of 2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal (Va) and the acetoxy group bonded to C1 of 1,2,3,4,5,6-hexa-O-acetyl-D-glucose S-ethyl monothioacetal (VIa) have been measured when the substrates were dissolved in solutions of acetic acid and acetic anhydride. The rate-determining step is interpreted to be the dissociation of the substrate conjugate acid to give a carbonium–sulfonium cation. The rate constants indicate that acyclic sugar derivatives are substituted faster than cyclic (pyranose) derivatives, and that an acetoxy group is substituted faster than an ethylthio group.

Substitution of acyclic sugar acetals. Perchloric acid catalyzed acetolysis of poly-O-acetyl acyclic oxygen and sulfur acetals and epimerization of monothioacetals

1967 ◽  
Vol 45 (13) ◽  
pp. 1467-1473 ◽  
Author(s):  
Norman H. Kurihara ◽  
Edgar Page Painter
Keyword(s):  
Acetic Acid ◽  
Perchloric Acid ◽  
Rate Constants ◽  
First Order ◽  
Acid Catalyzed ◽  
Pseudo First Order ◽  
Sugar Derivatives

The rate constants are reported for the substitution of acyclic sugar poly-O-acetyl diethyl dithioacetals, poly-O-acetyl diethyl acetals, and poly-O-acetyl dimethyl acetals and for the epimerization of poly-O-acetyl S-ethyl monothioacetals when catalyzed by perchloric acid in acetic acid. All the reactions are pseudo first order. Monothioacetals substitute faster than oxygen acetals, and oxygen acetals substitute faster than sulfur acetals. A group bonded to C1 of these acyclic sugar derivatives is substituted faster than when the group is bonded to C1 of poly-O-acetyl pyranose derivatives.

Perchloric acid catalyzed acylation of anisole

1976 ◽  
Vol 10 (3) ◽  
pp. 363-364
Author(s):  
B. M. Savin ◽  
S. A. Kesler
Keyword(s):  
Perchloric Acid ◽  
Acid Catalyzed
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