Oxidation for unsymmetrical bromo-1,10-phenanthrolines and subsequent hydroxylation, decarbonylation and chlorination reactions

A systematic investigation on the oxidation of unsymmetric bromo-phens is presented herein, where the reaction temperature is found to be the key parameter to generate oxidation or oxidation-bromination products. The regioselective C3-brominated compounds are produced in moderate yields in the cases...

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Bibliographic Details
Published inTetrahedron Vol. 74; no. 34; pp. 4495 - 4503
Main Authors Peng, Yu-Xin, Hu, Bin, Huang, Wei
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.08.2018
Elsevier
Subjects
Bromo-1,10-phenanthroline
Chemistry
Chemistry, Organic
Chlorination
Decarbonylation
Hydroxylation
Oxidation
Physical Sciences
Science & Technology
Oxidation
Chlorination
Hydroxylation
Decarbonylation
Bromo-1,10-phenanthroline
CONTAINING 1,10-PHENANTHROLINE LIGAND
DNA-BINDING
RHENIUM(I) COMPLEX
QUINONE CATALYST
RU(II) COMPLEXES
REDOX BEHAVIOR
RUTHENIUM
FLUORESCENCE
PHENANTHROLINE
N-ALKYLATION
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Summary:A systematic investigation on the oxidation of unsymmetric bromo-phens is presented herein, where the reaction temperature is found to be the key parameter to generate oxidation or oxidation-bromination products. The regioselective C3-brominated compounds are produced in moderate yields in the cases of 2-bromo-phen and 4-bromo-phen. Subsequent hydroxylation and decarbonylation for bromo-phds are also studied, where a series of bromo-diazafluorenones and phen-triones have been isolated. Furthermore, various chlorination products have been obtained by treating bromo-phds or bromo-phts with excess POCl3. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.07.015