Theoretical Explanation of Reaction Site Selectivity in the Addition of a Phenoxy Group to Perfluoropyridine.
Summary of "Theoretical Explanation of Reaction Site Selectivity in the Addition of a Phenoxy Group to Perfluoropyridine."
Pentafluoropyridine, a potentially useful precursor in organofluorine methodology, undergoes selective substitution of a fluorine with a phenoxide at the site para to the nitrogen. Subsequent aryloxide substitutions can be accomplished at the ortho positions with aryloxide groups containing various functional groups para to the phenoxide oxygen. During this phase of the reaction, "reverse reactions" involving substitutions of the original para substituent with a free fluoride or with another aryloxide moiety are observed with a frequency that depends on the functional group para to the oxy-gen on the aryloxide. Herein, we provide a theoretical explanation of these observations through use of density functional theory.
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Journal Details
This article was published in the following journal.
Name: The journal of physical chemistry. A
ISSN: 1520-5215
Pages:
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/31532671
- DOI: http://dx.doi.org/10.1021/acs.jpca.9b06413
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