Catalytic reaction of 3-phenyl-2-propyn-1-ol with alcohols (in Russian)
Journal Article
·
· J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6358127
The cyclic ketal 2,5-dimethyl-2,5-bis(3-phenyl-2-propynyloxy)-1,4-dioxane was obtained by the reaction of 3-phenyl-2-propyn-1=ol with propargyl alcohol in the presence of the HgO-BF/sub 3/ O(C/sub 2/H/sub 5/)/sub 2/ catalytic system. The transformation of 3-phenyl-2-propyn-1-ol and its ethers in methanol and ethanol by the action of the above-mentioned catalytic system leads to 1-phenyl-3-alkoxy-1-propanone, 1-phenyl-1,1,3-trialkoxypropane, and 1-phenyl-2-propen-1-one. The intermediate organomercury compound, which is the product from regioselective addition of mercuric oxide and the saturated alcohol at the triple bond, was isolated. Its protodemercuration led to the above-mentioned linear products. The formation of the cyclic ketal is presumably due to the preferred formation of mercury bis-hydroxypropargylide.
- Research Organization:
- All-Union Scientific-Research Institute of Chemical Reagents and Ultra-pure Chemicals, Erevan, USSR
- OSTI ID:
- 6358127
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:8; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- Russian
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Wed May 01 00:00:00 EDT 1996
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETONE
ALCOHOLS
ALKANES
BORON COMPOUNDS
BORON FLUORIDES
CATALYSIS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
DIOXANE
FLUORIDES
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
KETONES
KINETICS
MERCURY COMPOUNDS
MERCURY OXIDES
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PROPANE
REACTION INTERMEDIATES
REACTION KINETICS
YIELDS
400201* -- Chemical & Physicochemical Properties
ACETONE
ALCOHOLS
ALKANES
BORON COMPOUNDS
BORON FLUORIDES
CATALYSIS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
DIOXANE
FLUORIDES
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
KETONES
KINETICS
MERCURY COMPOUNDS
MERCURY OXIDES
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PROPANE
REACTION INTERMEDIATES
REACTION KINETICS
YIELDS