Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
Cyclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as a reagent followed b...
| Authors: | , , |
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| Format: | article |
| Status: | Published version |
| Publication Date: | 2016 |
| Country: | Argentina |
| Institution: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repository: | CONICET Digital (CONICET) |
| Language: | English |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/51621 |
| Online Access: | http://hdl.handle.net/11336/51621 |
| Access Level: | Open access |
| Keyword: | 1,4-Dicarbonyl Compounds Ketone Enolate Anions Dimerization https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Summary: | Cyclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as a reagent followed by subsequent double alkylation with bis-iodide yielding a cyclopentane adduct. This methodology allows the use of a simple potassium tert-butoxide as a base at room temperature for the formation of three C–C bonds resulting in a relatively complex five-membered ring diketone structure under transition-metal-free conditions. |
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