138835-32-2Relevant academic research and scientific papers
Strong phenyl-perfluorophenyl π-π stacking and C-H?F-C hydrogen bonding interactions in the crystals of the corresponding aromatic aldimines
Zhu, Shizheng,Zhu, Shifa,Jin, Guifang,Li, Zhanting
, p. 2713 - 2716 (2007/10/03)
The X-ray diffraction analysis of two co-crystals, 1?2 (aldimines 1 and 2) and 3?4 (aldimines 3 and 4), reveals that there are strong phenyl-perfluorophenyl π-π stacking and intermolecular hydrogen bonding interactions. The new perfluoroaryl-aryl face-to-face interaction of the crystalline aldimines provides a design motif for a new class of self-assembling system.
A new one-pot synthesis of 1,2,3,4-tetrafluoroacridines and some 7-substituted derivatives
Adamson, Adrian J.,Banks, Ronald E.,Tipping, Anthony E.
, p. 5 - 10 (2007/10/02)
1,2,3,4-Tetrafluoroacridine (1a) and a range of 7-substituted analogues can be synthesised by heating pre-formed Schiff bases (E)-C6F5CH=NC6H4R-p (3) (from C6F5CHO + H2NC6H4R-p) with the parent aniline H2NC6H4R-p (1:1 molar ratio) or by heating a mixture of the aldehyde C6F5CHO and the aniline H2NC6H4R-p (R=H, OMe, Me, But, F, Cl and Br) (1:2 molar ratio) in toluene or 1,2-dichlorobenzene under reflux.The mechanism has been deduced through the isolation in certain reactions of ortho-substituted Schiff bases 2-(p-RC6H4NH)C6F4CH=NC6H4R-p (6) (R=Cl or Br), which on acid catalysis (by p-RC6H4NH3(+)F(-)) undergo ring-closure with elimination of the aniline p-RC6H4NH2.Except where R=F, Cl or Br, substantial amounts of the corresponding 3-anilino-1,2,4-trifluoroacridines 5 are also formed; these arise via sequential para- and ortho-substitution of fluorine in the pentafluorophenyl moiety of the Schiff bases.The synthesis is capable of extension to other fluorinated aromatic aldehydes, e.g. the formation of 1-fluoro-7-methoxyacridine (9) from 2,6-difluorobenzaldehyde and p-anisidine.
