Photolysis of enol acetates and α-bromo derivatives ofo-(acyloxy)acetophenones

1985 ◽  
Vol 1985 (3) ◽  
pp. 589-598 ◽  
Author(s):  
Hermenegildo García ◽  
Roberto Martínez-Utrilla ◽  
Miguel A. Miranda
Keyword(s):  
Enol Acetates

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

2021 ◽  
Author(s):  
Vera A. Vil’ ◽  
Valentina M. Merkulova ◽  
Alexey I. Ilovaisky ◽  
Stanislav A. Paveliev ◽  
Gennady I. Nikishin ◽  
...  
Keyword(s):  
Electrochemical Synthesis ◽  
Enol Acetates

The photoaddition of 1,3-diketonatoboron difluorides with benzene derivatives

1991 ◽  
Vol 69 (3) ◽  
pp. 423-431 ◽  
Author(s):  
Yuan L. Chow ◽  
Xinxin Ouyang
Keyword(s):  
Crystallographic Analysis ◽  
Secondary Oxidation ◽  
Enol Ethers ◽  
X Ray ◽  
Thermal Reactions ◽  
Secondary Reactions ◽  
Enol Acetates ◽  
Orthogonal Orientation ◽  
Acid Catalyzed ◽  
Boron Difluoride

The boron difluoride complexes of 2-acetylcyclohexanone, 2-acetylcyclopentanone, and acetylacetone (abbreviated as ACHBF2, ACPBF2, and AABF2) were irradiated in the presence of benzene to give the 1:1 adducts as the primary photoadducts; for certain BF2 complexes, toluene, chlorobenzene, benzonitrile, and methyl benzoate were also used as substrates. The 1,5-diketone photoadducts were assumed to form by a [2+2] photocycloaddition followed by cyclobutane opening and hydrolysis to give 1,2 adducts. They undergo a variety of secondary thermal reactions, probably acid catalyzed, to give enol ethers, enol acetates, acetophenones, and ketonylacetophenones. The efficiency of these secondary reactions determines the final products. Photoaddition with a monosubstituted benzene preferentially occurs at the 3,4 bond without regioselectivity. Under oxygen, ACHBF2 photolytically reacts with benzene to give a secondary oxidation product of a 10-membered cyclic alkylphe-none, which is proven by X-ray crystallographic analysis to have the benzene ring and carbonyl group in orthogonal orientation. It is shown that the singlet excited state ACHBF2 initiates the photoaddition, probably through the formation of the benzene exciplex, which could be detected by its emission. While the Stern–Volmer rates are small, the quantum yield of photoaddition products is as high as 0.12–0.19 under limiting conditions. Key words: [2+2] photocycloaddition, non-planar alkanophenone, macrocyclic alkanophenone, boron difluoride complexes, photoaddition to benzenes.

Microbial hydroxylation of steroids. 6. Hydroxylation of C-6-substituted androst-4-ene-3,17-diones by Rhizopusarrhizus ATCC 11145

1979 ◽  
Vol 57 (13) ◽  
pp. 1585-1587 ◽  
Author(s):  
Herbert L. Holland ◽  
Peter R. P. Diakow
Keyword(s):  
Microbial Hydroxylation ◽  
Enol Acetates

The products arising from the incubations of C-6α and C-6β chloro-, fluoro-, and methyl-substituted Δ4-3-keto steroids with the C-6β hydroxylating fungus Rhizopusarrhizus ATCC 11145 have been identified, and their formation rationalised in terms of Δ3,5 enolic intermediates. The incubations of C-6 chloro and methyl Δ3,5 enol acetates with R. arrhizus, and the oxidations by m-chloroperoxybenzoic acid of the corresponding enol ethyl ethers have also been described. The relevance of the results so obtained to the mechanism of C-6β hydroxylation of Δ4-3-keto steroids by R. arrhizus is discussed.

ChemInform Abstract: A Novel Photochemical 1,4-Acyl Migration in Enol Esters. The Photolysis of Enol Acetates of 3-Phenylpropiophenones.

ChemInform ◽  
1988 ◽  
Vol 19 (3) ◽  
Author(s):  
M. ALVARO ◽  
V. BALDOVI ◽  
H. GARCIA ◽  
M. A. MIRANDA ◽  
J. PRIMO
Keyword(s):  
Acyl Migration ◽  
Enol Esters ◽  
Enol Acetates

scholarly journals Salicylic Acid‐Catalyzed Arylation of Enol Acetates with Anilines

2018 ◽  
Vol 360 (14) ◽  
pp. 2773-2778 ◽  
Author(s):  
Diego Felipe‐Blanco ◽  
Jose C. Gonzalez‐Gomez
Keyword(s):  
Salicylic Acid ◽  
Enol Acetates ◽  
Acid Catalyzed

Enol acetates of aldehydo sugar derivatives. Synthesis and crystallographic determination of double-bond geometry

1976 ◽  
Vol 41 (15) ◽  
pp. 2652-2653 ◽  
Author(s):  
Arnaud. Ducruix ◽  
Claudine. Pascard-Billy ◽  
Stephen J. Eitelman ◽  
Derek. Horton
Keyword(s):  
Double Bond ◽  
Enol Acetates ◽  
Sugar Derivatives

Functionalized Bis-enol Acetates as Specific Molecular Probes for Esterases

ChemBioChem ◽  
2013 ◽  
Vol 14 (18) ◽  
pp. 2435-2438 ◽  
Author(s):  
Phillipp Richter ◽  
Jerrit Weißflog ◽  
Natalie Wielsch ◽  
Aleš Svatoš ◽  
Georg Pohnert
Keyword(s):  
Molecular Probes ◽  
Enol Acetates
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