Reactivity of carbanions. XXIII. Wittig rearrangement of 9-fluorenol ethers under the conditions of phase-transfer catalysis

Journal Article · Wed Dec 09 23:00:00 EST 1987 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6289693

Solov'yanov, A A; Ahmed, E S.A.A.; Beletskaya, I P; Reutov, O A

The Wittig rearrangement of the phenyl, methyl, benzyl, and allyl ethers of 9-fluorenol was investigated under the conditions of phase-transfer catalysis in a system consisting of a solid powdered base and an organic phase. With the exception of the phenyl ether, which does not enter into the reaction, the rearrangement of all the ethers takes place by a dissociation-recombination mechanism with the formation of the fluorenone-migrating group carbanion pair as intermediate. The migratory aptitude increases in the order methyl < benzyl < allyl. The orders of effectiveness were established for the bases, phase-transfer catalysts, and solvents in the Wittig rearrangement.

• Research Organization: M.V. Lomonosov Moscow State Univ. (USSR)
• OSTI ID: 6289693
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:7; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical &amp; Physicochemical Properties
ACTIVATION ENERGY
ALCOHOLS
ALKALI METAL COMPOUNDS
ALKYLATING AGENTS
ANIONS
AROMATICS
CARBANIONS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHARGED PARTICLES
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CONDENSED AROMATICS
DISSOCIATION
ENERGY
ETHERS
FLUORENE
GLYCOLS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
HYDROXY COMPOUNDS
IONS
ISOMERIZATION
KINETICS
METHANOL
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC POLYMERS
OXYGEN COMPOUNDS
POLYETHYLENE GLYCOLS
POLYMERS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
REACTION INTERMEDIATES
REACTION KINETICS
RECOMBINATION
SYNTHESIS