Comparison of the Nitration of Polyfluoronitrobenzenes by Nitronium Salts in Superacidic and Aprotic Media: Activation of the Nitronium Ion by Protosolvation

The reactivity of nitronium tetrafluoroborate in the nitration of deactivated di- and trifluoronitrobenzenes is enhanced in superacidic trifluoromethanesulfonic (triflic) acid compared with aprotic methylene chloride and sulfolane solutions. The enhanced reactivity is discussed in terms of better so...

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Bibliographic Details
Published in:	Proceedings of the National Academy of Sciences - PNAS Vol. 89; no. 15; pp. 6670 - 6672
Main Authors:	Olah, George A., Laali, Kenneth K., Sandford, Graham
Format:	Journal Article
Language:	English
Published:	Washington, DC National Academy of Sciences of the United States of America 01-08-1992 National Acad Sciences National Academy of Sciences
Subjects:	Chemicals Chemistry Exact sciences and technology Ions Kinetics and mechanisms Nitration Nitrogen Organic chemistry Reactivity Reactivity and mechanisms Room temperature Salt Salts Solvents Solvent effect Nitro compound Nitration Solvation Superacid Benzenic compound Fluorine Organic compounds Aprotic solvent Comparative study
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Summary:	The reactivity of nitronium tetrafluoroborate in the nitration of deactivated di- and trifluoronitrobenzenes is enhanced in superacidic trifluoromethanesulfonic (triflic) acid compared with aprotic methylene chloride and sulfolane solutions. The enhanced reactivity is discussed in terms of better solubility and higher dissociation of the nitronium salts, as well as protosolvation of NO+2 by superacids.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0027-8424 1091-6490
DOI:	10.1073/pnas.89.15.6670