Mechanism of Acid-Catalyzed Epoxidation of Alkenes with Peroxy Acids

1997 ◽  
Vol 62 (15) ◽  
pp. 5191-5197 ◽  
Author(s):  
Robert D. Bach ◽  
Carlo Canepa ◽  
Julia E. Winter ◽  
Paul E. Blanchette
Keyword(s):  
Acid Catalyzed ◽  
Peroxy Acids ◽  
Epoxidation Of Alkenes

Transition structure for the epoxidation of alkenes with peroxy acids. A theoretical study

1991 ◽  
Vol 113 (6) ◽  
pp. 2338-2339 ◽  
Author(s):  
Robert D. Bach ◽  
Amy L. Owensby ◽  
Carlos Gonzalez ◽  
H. Bernard Schlegel ◽  
Joseph J. W. McDouall
Keyword(s):  
Theoretical Study ◽  
Transition Structure ◽  
Peroxy Acids ◽  
Epoxidation Of Alkenes

Oxidation of 3β,28-Diacetoxy-18-lupen-21-one with Peroxy Acids: A Way to Des-E-lupane Derivatives

1993 ◽  
Vol 58 (10) ◽  
pp. 2505-2516 ◽  
Author(s):  
Eva Klinotová ◽  
Martin Rejzek ◽  
Hana Zůnová ◽  
Jan Sejbal ◽  
Jiří Klinot ◽  
...  
Keyword(s):  
Alkaline Medium ◽  
Peracetic Acid ◽  
Lead Tetraacetate ◽  
Epoxy Derivative ◽  
Oxidative Removal ◽  
Acid Catalyzed ◽  
Peroxy Acids ◽  
Strong Acids

Oxidation of 3β,28-diacetoxy-18-lupen-21-one (I) and its 18β, 19β-epoxy derivative III with peracetic acid, catalyzed with strong acids, proceeds with cleavage of the bond between C-19 and C-21 under formation of E-seco derivatives with hydroxyl and isobutyryl groups on C-18 (spiro lactones V - VII and acid VIII). Oxidative removal of the isobutyryl fragment in spiro lactone VI by treatment with lead tetraacetate leads to the tetranor derivative - keto lactone XI which in an alkaline medium loses formaldehyde from C-17 to give des-E acid XVI.

A reinvestigation of the mechanism of epoxidation of alkenes by peroxy acids. A CASSCF and UQCISD study

2002 ◽  
Vol 43 (23) ◽  
pp. 4215-4219 ◽  
Author(s):  
Sergiy Okovytyy ◽  
Leonid Gorb ◽  
Jerzy Leszczynski
Keyword(s):  
Peroxy Acids ◽  
Epoxidation Of Alkenes

Acid Catalyzed Furan Ring Transposition

10.1039/sp768 ◽  
2014 ◽  
Author(s):  
Jamsheena V. ◽  
Ravindra Phatake
Keyword(s):  
Furan Ring ◽  
Acid Catalyzed

Three Carbon-Heteroatom Bonds: Esters and Lactones; Peroxy Acids and R(CO)OX Compounds; R(CO)X, X=S, Se, Te

2005 ◽  
Author(s):  
Y. R. Mahajan ◽  
S. M. Weinreb ◽  
D. Stien ◽  
T. Ziegler ◽  
D. J. Austin ◽  
...  
Keyword(s):  
Peroxy Acids

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

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