1146-66-3Relevant articles and documents
Photoassisted Charge Transfer Between DMF and Substrate: Facile and Selective N,N-Dimethylamination of Fluoroarenes
Ansari, Tharique N.,Sharma, Sudripet,Bora, Pranjal P.,Ogulu, Deborah,Parmar, Saurav,Gallou, Fabrice,Kozlowski, Pawel M.,Handa, Sachin
, p. 2704 - 2709 (2021/06/09)
A reversible Van der Waals complex formation between the electron-deficient fluorinated aromatic ring and N,N-dimethylformamide (DMF) molecules followed by light irradiation resulted in charge transfer (CT) process. The complex was stabilized by ammonium formate and further decomposed to form the C?N bond. Control experiments revealed that the simultaneous SNAr pathway also contributes to product formation. This methodology is mild, metal-free, and effective for the amination of a variety of substrates. The reproducibility of this methodology was also verified on gram-scale reactions. The CT states were supported by control UV/Vis spectroscopy and computational studies.
PARTIALLY FLUORINATED HETEROCYCLIC COMPOUNDS. PART 24. A PLAUSIBLE MECHANISM FOR THE FORMATION OF THE FISCHER INDOLE PRODUCT FROM ACETOPHENONE 1,3,4,5,6,7,8,-HEPTAFLUORO-2-NAPHTHYLHYDRAZONE IN WHICH o-FLUORINE IS LOST
Brooke, Gerald M.
, p. 51 - 58 (2007/10/02)
Acetophenone 1,3,4,5,6,7,8,-heptafluoro-2-naphthylhydrazone (1) reacts in tetralin at reflux to give 4,5,6,7,8,9,-hexafluoro-2-phenylbenzindole (2) as the major product, accompanied by other materials including acetophenone 3,4,5,6,7,8,-hexafluoro-2-naphthylhydrazone (4) which is proposed as the true precursor to the Fischer indole product (2) since it gives (2) under the same conditions.The presence of α-tetralone in the reaction mixture provides the clue to a reductive elimination of F- from (1).
Partially Fluorinated Heterocyclic Compounds. Part 18. Formation of Fischer Indole Products from Acetophenone 1,3,4,5,6,7,8-Heptafluoro-2-naphthylhydrazone and Acetophenone Pentafluorophenylhydrazone. The Surprising Loss of o-Fluorine
Brooke, Gerald M.
, p. 821 - 826 (2007/10/02)
Acetophenone 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazone (2) and acetophenone pentafluorophenylhydrazone (3) react in tetralin at reflux temperature to give among the products 4,5,6,7,8,9-hexafluoro-2-phenylbenzindole (6) and 4,5,6,7-tetrafluoro-2-ph