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Intramolecular Nucleophilic Displacement of Fluorine
Author(s) -
Hudlicky M.
Publication year - 1978
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197800011
Subject(s) - chemistry , geminal , intramolecular force , nucleophile , fluorine , phenols , aromaticity , nucleophilic aromatic substitution , medicinal chemistry , molecule , organic chemistry , nucleophilic substitution , catalysis
Intramolecular nucleophilic displacement in organic fluorine compounds takes place if a fluorine atom is located in the molecule at such a distance from a nucleophilic functional group as to allow cyclization to three‐membered rings (in aliphatic compounds only), five‐membered rings, six‐membered rings, and, exceptionally, seven‐ and polymembered rings (in aromatic series only). The nucleophilic functions can be hydroxyl groups of alcohols, enols, phenols and carboxylic acids, sulfhydryl groups, primary or secondary amino groups, and carbanionic carbon atoms. The reaction is common with aliphatic monofluorides and aromatic polyfluorides, and rare with geminal and trigeminal fluorides. Whereas in the aliphatic series it is usually an undesirable side‐reaction, in the aromatic series it is useful as a means of synthesizing carbocyclic and heterocyclic polynuclear compounds.