1,3-Dimethyl-2-phenylbenzimidazoline (DMPBI)-Acetic Acid: An Effective Reagent System for Photoinduced Reductive Transformation of α,β-Epoxy Ketones to β-Hydroxy Ketones

Synthesis ◽  
2004 ◽  
Vol 112 (08) ◽  
Author(s):  
Eietsu Hasegawa ◽  
Naoki Chiba ◽  
Aiko Nakajima ◽  
Kumiko Suzuki ◽  
Akira Yoneoka ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Reductive Transformation ◽  
Hydroxy Ketones ◽  
Epoxy Ketones

CHEMO- AND REGIOSELECTIVE REDUCTION OF α,β-EPOXY KETONES TO β-HYDROXY KETONES BY SODIUM HYDROGENTELLURIDE

1984 ◽  
Vol 13 (2) ◽  
pp. 271-272 ◽  
Author(s):  
Atsuhiro Osuka ◽  
Koji Taka-Oka ◽  
Hitomi Suzuki
Keyword(s):  
Hydroxy Ketones ◽  
Epoxy Ketones

Photochemistry of a-diketones. I. Some photochemical reactions of 1,1,4,4-Tetramethyl-2,3-dioxotetralin

1967 ◽  
Vol 20 (8) ◽  
pp. 1671 ◽  
Author(s):  
GE Gream ◽  
JC Paice ◽  
CCR Ramsay
Keyword(s):  
Carbon Monoxide ◽  
Acetic Acid ◽  
Carbonyl Group ◽  
Methyl Formate ◽  
Photochemical Reactions ◽  
Hydroxy Ketones ◽  
Competing Reactions

The photochemical reactions (at λ > 3000 A) of the non-enolizable α- diketone (XIV) have been investigated in the solvents methanol, isopropanol. cyclohexane, toluene, n-butyraldehyde, methyl formate, acetic acid, dioxan, and benzene. In general, selective 1,2-addition of solvent to one carbonyl group to give a-hydroxy ketones is the predominant reaction. Competing reactions include reduction to the acyloin (XXI) and loss of carbon monoxide to give 1,1,3,3- tetramethylindanone (XVII). In methanol, two isomeric diols (XXIII) and (XXIV) were unexpectedly formed.

Hydrazine Hydrate Induced Reductive Cleavage of α,β-Epoxy Ketones: An Efficient Procedure for the Preparation of β-Hydroxy Ketones.

ChemInform ◽  
2005 ◽  
Vol 36 (22) ◽  
Author(s):  
Jorge A. R. Salvador ◽  
Alcino J. L. Leitao ◽  
M. Luisa Sa e Melo ◽  
James R. Hanson
Keyword(s):  
Hydrazine Hydrate ◽  
Reductive Cleavage ◽  
Efficient Procedure ◽  
Hydroxy Ketones ◽  
Epoxy Ketones

scholarly journals Catalytic Hydrogenation of α,β-Epoxy Ketones to Form β-Hydroxy Ketones Mediated by an NADH Coenzyme Model.

ChemInform ◽  
2006 ◽  
Vol 37 (49) ◽  
Author(s):  
Hua-Jian Xu ◽  
You-Cheng Liu ◽  
Yao Fu ◽  
Yun-Dong Wu
Keyword(s):  
Catalytic Hydrogenation ◽  
Hydroxy Ketones ◽  
Epoxy Ketones

The Conversion of Levoglucosenone into Isolevoglucosenone

2015 ◽  
Vol 68 (4) ◽  
pp. 593 ◽  
Author(s):  
Xinghua Ma ◽  
Natasha Anderson ◽  
Lorenzo V. White ◽  
Song Bae ◽  
Warwick Raverty ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Single Crystal ◽  
Lignocellulosic Biomass ◽  
Allylic Alcohol ◽  
Allylic Alcohols ◽  
Alkaline Hydrogen Peroxide ◽  
X Ray ◽  
Epoxy Ketones ◽  
Epoxy Alcohols

Levoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.

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