694-02-0Relevant articles and documents
Dynamic NMR Study of Cyclopropylcarbonyl Fluoride. A Comparison of the Conjugating Abilities of the Cyclopropyl, Vinyl, and Phenyl Groups
Noe, Eric A.,Young, Rose M.
, p. 6218 - 6220 (1982)
Rotation about the bond between the COF group and C-1 of cyclopropylcarbonyl fluoride is slow on the NMR time scale at -163 deg C.The fluorine NMR spectrum at this temperature shows signals for two conformations, which have nearly identical free energies.A free energy barrier of 5.5 +/- 0.2 kcal/mol was calculated for interconversion of isomers at -134 deg C.Comparison of this barrier with the rotational barriers for acryloyl fluoride and benzoyl fluoride indicates that the ?-donating abilities of the vinyl and cyclopropyl groups are nearly equal and are lower than for phenyl, at least with the fluorocarbonyl group as the ? acceptor.
Acyl fluorides from carboxylic acids, aldehydes, or alcohols under oxidative fluorination
Liang, Yumeng,Zhao, Zhengyu,Taya, Akihito,Shibata, Norio
supporting information, p. 847 - 852 (2021/02/06)
We describe a novel reagent system to obtain acyl fluorides directly from three different functional group precursors: carboxylic acids, aldehydes, or alcohols. The transformation is achieved via a combination of trichloroisocyanuric acid and cesium fluoride, which facilitates the synthesis of various acyl fluorides in high yield (up to 99%). It can be applied to the late-stage functionalization of natural products and drug molecules that contain a carboxylic acid, an aldehyde, or an alcohol group.
Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids
Hoerrner, Megan E.,Wang, Jiang,Watson, Mary P.,Weix, Daniel J.
supporting information, p. 13484 - 13489 (2020/06/10)
While ketones are among the most versatile functional groups, their synthesis remains reliant upon reactive and low-abundance starting materials. In contrast, amide formation is the most-used bond-construction method in medicinal chemistry because the che
Synthesis of acyl fluorides via photocatalytic fluorination of aldehydic C-H bonds
Meanwell, Michael,Lehmann, Johannes,Eichenberger, Marc,Martin, Rainer E.,Britton, Robert
supporting information, p. 9985 - 9988 (2018/09/11)
Acyl fluorides are versatile acylating agents owing to their unique stability. Their synthesis, however, can present challenges and is typically accomplished through deoxyfluorination of carboxylic acids. Here, we demonstrate that acyl fluorides can be prepared directly from aldehydes via a C(sp2)-H fluorination reaction involving the inexpensive photocatalyst sodium decatungstate and electrophilic fluorinating agent N-fluorobenzenesulfonimide. This convenient fluorination strategy enables direct conversion of aliphatic and aromatic aldehydes into acylating agents.
Carbon-chain isomerization during the electrochemical fluorination in anhydrous hydrogen fluoride - A mechanistic study
Ignat'ev, Nikolai V.,Welz-Biermann, Urs,Heider, Udo,Kucheryna, Andriy,von Ahsen, Stefan,Habel, Wolfgang,Sartori, Peter,Willner, Helge
, p. 21 - 37 (2007/10/03)
The compounds i-C4H9SO2F, i-C3H7SO2F and cyclo-C3 H7C(O)F have been subjected to electrochemical fluorination in anhydrous hydrogen fluoride. The resulting products were fully analyzed by NMR spectroscopy. From the reaction balances, literature data and quantum chemical calculations, a new mechanism for carbon-chain isomerization during the electrochemical fluorination (ECF) is proposed. The key step in the formation of isomeric products is believed to be a ring closure reaction involving carbo-cationic or biradical intermediates.
Use of the potassium ion as a template for the selective derivatization of the antibiotic X-206
O'Sullivan, Anthony C.,Struber, Fritz,Ley, Steven V.
, p. 6252 - 6256 (2007/10/03)
The templating effect of potassium ions on the ionophore antibiotic X- 206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) p
