77976-05-7Relevant articles and documents
Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles
Barbasiewicz, Micha?,Tryniszewski, Micha?
, (2021/11/30)
A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7-20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.
The Relationship between 19F Substituent Chemical Shifts and Electron Densities: meta- and para-Substituted Benzoyl Fluorides
Brownlee, Robert T. C.,Craik, David J.
, p. 186 - 191 (2007/10/02)
The 19F substituent chemical shifts (SCS) of meta- and para-benzoyl fluorides are found to correlate well with substituent parameters using the dual substituent parameter (DSP) equation, indicating that they reflect electronic perturbations induced by the substituent.The direction of the SCS values is such that donating substituents cause upfield shifts whilst acceptors cause downfield shifts.STO-3G calculations indicate that substituents induce only very small changes in ?-electron density about the fluorine atom, but that these changes correlate reasonably well with the observed SCS values.For the para series, the slope of the relationship between Δq?F and 19F SCS is 5000 ppm/electron, indicating the great sensitivity of the fluorine atom to small changes in electron density.
