Catalytic reaction of 3-phenyl-2-propyn-1-ol with alcohols

Journal Article · Sat Jan 10 00:00:00 EST 1987 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6358127

Grigoryan, S G; Avetisyan, K G; Matnishyan, A A

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), Vol. 22:8; Other Information: Translated from Zh. Org. Khim.; 22: No. 8, 1587-1591(Aug 1986)
• Country of Publication: United States
• Language: Russian

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ALCOHOLS
CATALYSIS
BORON FLUORIDES
CATALYTIC EFFECTS
MERCURY OXIDES
ACETONE
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
DIOXANE
ORGANOMETALLIC COMPOUNDS
PROPANE
REACTION INTERMEDIATES
ALKANES
BORON COMPOUNDS
CHALCOGENIDES
FLUORIDES
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
KETONES
KINETICS
MERCURY COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
REACTION KINETICS
YIELDS
400201* - Chemical & Physicochemical Properties