Cover Picture: Positioning a Carbon-Fluorine Bond over the [pi]Cloud of an Aromatic Ring: A Different Type of Arene Activation

Through-space arene activation is described by T. Lectka etal. in their Communication on page8266ff. Anchimeric assistance by a C-F bond positioned rigidly over an arene molecule strongly activates the ring toward electrophilic nitration. The lone electron pairs of fluorine effect stabilization of t...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 55; no. 29; p. 8137
Main Authors Holl, Maxwell Gargiulo, Struble, Mark D, Singal, Prakhar, Siegler, Maxime A, Lectka, Thomas
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 11.07.2016
EditionInternational ed. in English
Subjects
Activation
Carbon
Fluorine
Ice
Nitration
Stabilization
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Summary:Through-space arene activation is described by T. Lectka etal. in their Communication on page8266ff. Anchimeric assistance by a C-F bond positioned rigidly over an arene molecule strongly activates the ring toward electrophilic nitration. The lone electron pairs of fluorine effect stabilization of the transition state that leads to the arenium intermediate. In the picture, the C-F bond (human figure above the ice) reaches through the aromatic ring to assist the nitronium figure submerged below.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201604537