1969/09/22 · 2 citations
Pharmacology, Toxicology and Pharmaceutics · #Fluorine in Organic Chemistry
paper · doi:10.1021/cen-v047n040.p045
crossref issued 1969/09/22 · crossref published 1969/09/22 · crossref published-print 1969/09/22 · openalex publication_date 1969/09/22 · crossref published-online 2010/11/12 · crossref created 2010/11/12 · crossref deposited 2023/04/05 · openalex created_date 2025/10/10 · crossref indexed 2026/07/29 · openalex updated_date 2026/07/30
The novel compound xenon difluoride (XeF 2 ) offers an attractive and apparently general means of fluorinating aromatic rings, M. J. Shaw of Argonne National Laboratory told fluorine chemists at the ACS national meeting. To fluorinate a ring and preserve aromaticity, preliminary substitution with nitro groups, reduction, and diazotization are usually required. Dr. Shaw and his associates, Dr. J. A. Weil and Dr. H. H. Hyman at Argonne and Dr. R. Filler at Illinois Institute of Technology, have found high substitution yields with XeF 2 and a number of aromatics. Xenon difluoride reacts with benzene to produce 68% fluorobenzene. Substituted benzenes react in the same way. Yields of mono substitution products range from 32% in the case of toluene to 76% for benzotrifluoride. Directive effects of substituents on the starting materials parallel those in electrophilic substitution reactions and in substitution reactions involving radical cations. For example, reaction of fluorobenzene with XeF2 gives 11.8% ortho-, 2.8% meta-, and 32.3% para-difluorobenzenes. Benzotrifluoride and XeF2 react to give 72% fluorobenzotrifluoride. ...