Syntheses of dibenzo[b,e][1,4]dioxin derivatives via iron complexes, and further functionalizations via directed metallation
| Autor: | Peter S. Rutledge, Richard C. Cambie, Sally J. Janssen, Paul D. Woodgate |
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| Rok vydání: | 1991 |
| Předmět: |
chemistry.chemical_classification
medicine.drug_class Stereochemistry Carboxylic acid Organic Chemistry Carboxamide Biochemistry Aldehyde Medicinal chemistry Inorganic Chemistry Deprotonation chemistry Cyclopentadienyl complex Nucleophilic aromatic substitution Electrophile Materials Chemistry Ultraviolet light medicine Physical and Theoretical Chemistry |
| Zdroj: | Journal of Organometallic Chemistry. 420:387-418 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/0022-328x(91)86467-5 |
| Popis: | Double nucleophilic aromatic substitution reactions between (cyclopentadienyl)(η 6 -1,2-dichlorobenzene)iron(1 + ) salts and substituted 1,2benzenediols have been carried out under mild conditions to prepare [η 6 -dibenzo[ b , e ][1,4]dioxin]iron(1 + ) complexes functionalized in the 1- or 2-position with an alkyl, aldehyde, carboxylic acid, methoxycarbonyl, carboxamide, or hydroxy group. 3-Methyl- and 4-methyl-(η 6 -1,2-dichlorobenzene)iron complexes were treated with substituted 1,2-benzenediols to effect functionalization of both aromatic rings of the heterocycle. The dibenzodioxin ligands were liberated routinely by irradiation with ultraviolet light. Directed deprotonation of the free functionalized dibenzodioxins with an alkyllithium reagent followed by quenching with a variety of electrophiles yielded further derivatives, including two new isoindolone systems. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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