Study of the Reactions of Fluorine‐Containing Amides with Aldehydes and the Structures of the Bisamides

Abstract

The reactions of trifluoro or bromodifluoro acetamides with aromatic aldehydes in the presence of thionyl chloride and trifluoromethylsulfonic acid were investigated. Compared with the procedure reported previously, the yields were improved greatly and the reaction conditions were much milder. Both intra-and intermolecular weak interactions were discussed in detail based on the X-ray diffraction analysis of 3aa and 3ab.

Where Does the Fluorine Come From? A Review on the Challenges Associated with the Synthesis of Organofluorine Compounds

“…72 EBDFA is prepared through bromination of chlorotrifluoroethylene followed by hydrolysis under strong acidic conditions (Scheme 4). 73 Methyl fluorosulfonyldifluoroacetate (MFDA) is an air and moisture stable and relatively low cost building block originally developed for trifluoromethylation of alkenes, aromatics, and amides. 74 It is also used as a difluorocarbene precursor for the synthesis of difluorocyclopropane 75 and is readily prepared through a [2 + 2] addition of tetrafluoroethylene with SO 3 and subsequent esterification (Scheme 5).…”

1,4-Diphenyl-1,3-butadiene and 1,1,4,4-Tetraphenyl-1,3-butadiene in the Reactions of Oxidative Sulfamidation and Trifluoroacetamidation

“…Of most interest is the splitting of one of the two double bonds of diene 1 with the formation of N,N′ ‐(phenylmethanediyl)bis(trifluoroacetamide) 11 . Product 11 is a known compound, which was prepared by the reaction of trifluoroacetamide with benzaldehyde and thionyl chloride catalyzed by triflic acid, and its structure was proved by X‐ray analysis . The structure of product 11 isolated by us from the reaction in Scheme was proved by the presence of a triplet of methine proton at 6.7 ppm, a doublet of NH protons and a multiplet of aromatic protons in the ratio of 1:2:5.…”