Reaction or ethyl diazoacetate with halogenoethylenes in the presence of rhodium(II) pivalate

In the presence of rhodium(II) pivalate, ethyl diazoacetate reacted with vinylidene chloride, vinyl bromide and cis-1,2-dichloroethylene to afford the corresponding cyclopropane carboxylates, but tetrachloroethylene, trichloroethylene and trans-1,2-dichloroethylene did not undergo cyclopropanation....

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 262; no. 1; pp. 85 - 88
Main Author Milner, David J.
Format Journal Article
LanguageEnglish
Published Lausanne Elsevier B.V 01.01.1984
Elsevier Science
Subjects
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
Cyclopropanation
Substituent effect
Catalytic reaction
Carboxylic acid
Reaction orientation
Rhodium II Compounds
Trans stereoisomer
Saturated compound
Dichloromethane
Halocarbon
Monocyclic compound
Cis stereoisomer
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Summary:In the presence of rhodium(II) pivalate, ethyl diazoacetate reacted with vinylidene chloride, vinyl bromide and cis-1,2-dichloroethylene to afford the corresponding cyclopropane carboxylates, but tetrachloroethylene, trichloroethylene and trans-1,2-dichloroethylene did not undergo cyclopropanation. These results indicate that cyclopropane carboxylates were accessible only from those halogenoethylenes having an unsubstituted end or side.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(00)99126-5