Oxidative acetoxylation of the silyl ethers of ketone enols

Journal Article · Wed Jul 20 04:00:00 EDT 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5887539

Brunovlenskaya, I I; Kusainova, K M; Kashin, A K

The authors studied the reaction of (dicarboxyiodo)benzenes with the trimethylsilyl ethers of ketone enols having various structures. They also undertook a comparative investigation of the oxidation of these compounds with lead tetraacetate. The reaction of (diacetoxyiodo)benzene with the trimethylsilyl ethers of ketone enols takes place with retention of the (CH/sub 3/)/sub 3/Si group in two directions, i.e., substitution of the vinylic hydrogen or diacetoxylation of the double bond. The reaction can be used for the regioselective synthesis of /alpha/-acetoxy ketones, since the trimethylsilyl group is readily eliminated from the obtained products by the action of fluoride ion or boron trifluoride etherate with the formation of the corresponding substituted ketones.

• OSTI ID: 5887539
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:2; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETATES
ACETONE
ACETOPHENONE
ACTIVATION ENERGY
ALCOHOLS
AROMATICS
BORON COMPOUNDS
BORON FLUORIDES
CAMPHOR
CARBOXYLIC ACID SALTS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CYCLOHEXANONE
ENERGY
ENOLS
ETHERS
FLUORIDES
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED AROMATIC HYDROCARBONS
HYDROXY COMPOUNDS
IODINATED AROMATIC HYDROCARBONS
KETONES
KINETICS
LEAD COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SILICON COMPOUNDS
OXIDATION
REACTION KINETICS
TERPENES
YIELDS