Sulfur Ylides. Communication 1. Cyclopropanation of. cap alpha. ,. beta. -unsaturated Ketones with Ethyl (dimethylsulfuranylidene) acetate generated in the presence of phase-transfer catalysts
Journal Article
·
· Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)
OSTI ID:6968363
This paper presents a modified method for the cyclopropanation of alpha, beta-unsaturated ketones with ethyl (dimethylsulfuranylidene) acetate, generated in situ from a sulfonium salt with 85% KOH in the presence of a phase-transfer catalyst, and studies the sterochemistry of the polysubstituted cyclopropanes. The chemical shifts of the carbon atoms of the cyclopropane rings of the isomer pairs are close together in the C 13 NMR spectra, which makes the assignment of the signals of C/sup 2/ and C/sup 3/ and the sterochemical assignment of each isomer to the cis and the trans series difficult. It is shown that the signals of the carboxyl carbon atoms differ not more than 0.65 ppm in the isomer pairs.
- Research Organization:
- Institute of Chemistry, Bashkir Branch, Acad of Sci., Ufa
- OSTI ID:
- 6968363
- Journal Information:
- Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 34:10,PT.1; ISSN BACCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETATES
ALCOHOLS
ALKALI METAL COMPOUNDS
ALKANES
CARBON
CARBOXYLIC ACID SALTS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
ELEMENTS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
HYDROXY COMPOUNDS
KETONES
KINETICS
NMR SPECTRA
NONMETALS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
PHASE TRANSFORMATIONS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
PROPANE
PROPANOLS
REACTION KINETICS
SPECTRA
SULFONATES
SULFUR COMPOUNDS
YIELDS
400201* -- Chemical & Physicochemical Properties
ACETATES
ALCOHOLS
ALKALI METAL COMPOUNDS
ALKANES
CARBON
CARBOXYLIC ACID SALTS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
ELEMENTS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
HYDROXY COMPOUNDS
KETONES
KINETICS
NMR SPECTRA
NONMETALS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
PHASE TRANSFORMATIONS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
PROPANE
PROPANOLS
REACTION KINETICS
SPECTRA
SULFONATES
SULFUR COMPOUNDS
YIELDS