Effect of the solvent on the stereochemistry of the mercuration of cyclopropene compounds and the product ratio (in Russian)
The stereochemistry of the addition of mercury salts to cyclopropene compounds is a problem of the solvomercuration reaction which the authors have tried to resolve in earlier work. In that work they showed that the reaction of a cyclic olefin with mercuric trifluoroacetate in methanol gives two stereoisomers in a ratio of 85 to 15. In this paper they establish that the replacement of methanol by acetic acid leads to fundamental changes both in the stereochemistry of addition and in the composition of the reaction products. Acetic acid gives two products. Both compounds, methyl 2-chloromercurio-3-trifluoroacetoxy-2,3-diphenylcyclopropane-1-carboxylate and methyl 2-chloromercurio-3-acetoxy-2,3-diphenylcyclopropane-carboxylate, are formed as a result of cis-addition in a ratio of 87 to 13. The NMR spectra and spin-spin coupling constants are given for both products.
- Research Organization:
- M. V. Lomonosov Moscow State Univ., USSR
- OSTI ID:
- 6136965
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:4; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- Russian
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Related Subjects
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ACETIC ACID
ALCOHOLS
ALKENES
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE COMPOUNDS
COMPARATIVE EVALUATIONS
COMPLEXES
COMPLEXOMETRY
CYCLOALKENES
ESTERS
FLUORINATED ALIPHATIC HYDROCARBONS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
HYDROXY COMPOUNDS
ISOMERIZATION
MATERIALS TESTING
MERCURY CHLORIDES
MERCURY COMPLEXES
MERCURY COMPOUNDS
MERCURY HALIDES
METHANOL
MONOCARBOXYLIC ACIDS
NMR SPECTRA
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SOLVENTS
SOLVENT PROPERTIES
SOLVENTS
SPECTRA
STEREOCHEMISTRY
SYNTHESIS
TESTING