Sequential Nucleophilic Aromatic Substitution Reactions of Activated Halogens

Building blocks have been identified that can be functionalised by sequential nucleophilic aromatic substitution. Some examples are reported that involve the formation of cyclic benzodioxin and phenoxathiine derivatives from 4,5-difluoro-1,2-dinitrobenzene, racemic quinoxaline thioethers, and sulfon...

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Bibliographic Details
Published in:International journal of molecular sciences 2024-08, Vol.25 (15), p.8162
Main Authors: Plater, M John, Harrison, William T A
Format: Article
Language:English
Subjects:
activated halogen
Amines
Asymmetry
Crystal structure
Crystallography, X-Ray
Dioxins
fluorine
Halogens - chemistry
Models, Molecular
Molecular Structure
nitro group
nucleophilic substitution
Oxidation
Quinoxalines - chemistry
Substitution reactions
sulphur–nitrogen chemistry
Symmetry
Citations: Items that this one cites
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Summary:Building blocks have been identified that can be functionalised by sequential nucleophilic aromatic substitution. Some examples are reported that involve the formation of cyclic benzodioxin and phenoxathiine derivatives from 4,5-difluoro-1,2-dinitrobenzene, racemic quinoxaline thioethers, and sulfones from 2,3-dichloroquinoxaline and (2-aminophenylethane)-2,5-dithiophenyl-4-nitrobenzene from 1-(2-aminophenylethane)-2-fluoro-4,5-dinitrobenzene. Four X-ray single-crystal structure determinations are reported, two of which show short intermolecular N-O N "π hole" contacts.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms25158162