ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Syntheses of New Aromatic Compounds with Fluorimated Side Chains and their Chemical ReactivityThe syntheses of a wide range of aromatic compounds of the type p-Y-C6H4CF2X (4-13) are described, and the chemical behavior of these compounds as a function of substituent Y is investigated [Y = both electron-releasing and -withdrawing substituents such as NO2, CF3, Cl, H, C(CH3)3, OCH3, and N(CH3)2 (a-g), X = -H, -Br, -SPh, -OPh, -N3, -NCO, -NCS, -SCN, -NCSe, or -SeCN]. Analogously the pyridine derivatives 15, 17, and 18 were synthesized and characterized. From a correlation of the 19F-NMR data of these compounds with the Hammett constant of Y, participation of C-F π-back-donation is seen as the cause for an observed shift of the 19F signals to lower field.
Notes:
Die Synthese zahlreicher Verbindungen des Typs p-Y-C6H4CF2X (4-13) wird beschrieben und ihr chemisches Verhalten in Abhängigkeit vom Substituenten Y untersucht [Y = Donor- und Akzeptorsubstituenten NO2, CF3, Cl, H, C(CH3)3, OCH3 und N(CH3)2 (a-g), X = -H, -Br, -SPh, -OPh, -N3, -NCO, -NCS, -SCN, -NCSe oder -SeCN]. Analog sind die Pyridinderivate 15, 17 und 18 dargestellt und charakterisiert worden. Durch Korrelation der 19F-NMR-Daten dieser Verbindungen gegen die Hammettkonstante des Y-Substituenten kann die Beteiligung von C-F-π-Rückbindungen als Ursache für eine Tieffeld-Signalverschiebung abgeleitet werden.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19881210718
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