Novel generation of phenylsulfenium ion and aromatic phenylthiolation. Reactions of hydrazoic acid, alkyl azides and hydroxylamine derivatives with alkyl phenyl sulfides in the presence of both trifluoromethanesulfonic acid and trifluoroacetic acid

1992 ◽  
Vol 0 (12) ◽  
pp. 916-917 ◽  
Author(s):  
Hiroshi Takeuchi ◽  
Takehiro Yanase ◽  
Katsutaka Itou ◽  
Hiromi Ōya ◽  
Taki Adachi
Keyword(s):  
Trifluoroacetic Acid ◽  
Trifluoromethanesulfonic Acid ◽  
Hydrazoic Acid ◽  
Alkyl Azides ◽  
Hydroxylamine Derivatives

Synthesis of Novel Isoquinolino[5,4-ab]phenanthridine Derivatives via Pictet–Spengler Reaction

Synthesis ◽  
2018 ◽  
Vol 51 (06) ◽  
pp. 1377-1382
Author(s):  
Tzenge-Lien Shih ◽  
Min-Chen Tsai ◽  
Pei Huang ◽  
Liang Syu
Keyword(s):  
Phosphoric Acid ◽  
Trifluoroacetic Acid ◽  
Trifluoromethanesulfonic Acid ◽  
Acidic Media

The reaction of 5-amino-2-[2-(dimethylamino)ethyl]-6-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione with a series of aldehydes in acidic media (phosphoric acid, trifluoromethanesulfonic acid, and trifluoroacetic acid) is described. This key step is based on the Pictet–Spengler reaction to synthesize ten novel isoquinolino[5,4-ab]phenanthridine derivatives. The most effective acid is phosphoric acid and optimized yields were obtained. The frameworks of target compounds are unique and have never been reported.

Acidity dependence of the trifluoromethanesulfonic acid catalyzed isobutane-isobutylene alkylation modified with trifluoroacetic acid or water

1996 ◽  
Vol 146 (1) ◽  
pp. 107-117 ◽  
Author(s):  
George A. Olah ◽  
Patrice Batamack ◽  
Denis Deffieux ◽  
Béla Török ◽  
Qi Wang ◽  
...  
Keyword(s):  
Trifluoroacetic Acid ◽  
Trifluoromethanesulfonic Acid ◽  
Acid Catalyzed

Organothallium Compounds. XV. Thallation of Polyfluoroaromatic Compounds

1979 ◽  
Vol 32 (4) ◽  
pp. 737 ◽  
Author(s):  
GB Deacon ◽  
D Tunaley
Keyword(s):  
Trifluoroacetic Acid ◽  
Sodium Acetate ◽  
Room Temperature ◽  
Sodium Iodide ◽  
Trifluoromethanesulfonic Acid ◽  
Boiling Water ◽  
Similar Reaction ◽  
Aqueous Sodium ◽  
Organothallium Compounds

Thallic trifluoromethanesulfonate has been prepared by reaction of trifluoromethanesulfonic acid with either thallic oxide or solutions of thallic trifluoroacetate in trifluoroacetic acid, and has been isolated as the trihydrate on crystallization fromnitromethane. The polyfluoroarenes,p-CH3OC6F4H, p-CH3C6F4H, m-H2C6F4, o-H2C6F4, p-H2C6F4, C6F5H, 1,3,5-F3C6H3 or 1,2,4-F3C6H3, have been thallated by thallic trifluoromethanesulfonate in trifluoroacetic acid, giving the corresponding poly- fluorophenylthallium(III) bis(trifluoromethanesulfonates), which have been characterized spectroscopically and by conversion into the corresponding (polyfluoro)iodobenzenes on treatment with sodium iodide. Only slight thallation of m-BrC6F4H and m-O2NC6F4H was observed. By contrast with thallic trifluoromethanesulfonate, thallic trifluoroacetate in trifluoroacetic acid induced little thallation of the most reactive polyfluorobenzene, p-CH3OC6F4H. Thallic trifluoromethanesulfonate also thallated p-CH3OC6F4H in nitromethane, sulfolane, and with the substrate as solvent, but p-CH3C6F4H failed to react. Treatment of the polyfluorophenylthallium(III) bis(trifluoromethane- sulfonates) with boiling aqueous sodium acetate caused symmetrization into the corresponding acetatobis(polyfluorophenyl)thallium(III) compounds. A similar reaction between 2,4,6-trifluoro- phenylthallium(III) bis(trifluoromethanesulfonate) and sodium acetate at room temperature yielded 2,4,6-trifluorophenylthallium(III) diacetate. 2,3,4,6-Tetrafluorophenylthallium(III) bis(trifluor0- methanesulfonate) was converted by boiling water into bis(2,3,4,6-tetrafluorophenyl)thallium(III) trifluoromethanesulfonate.

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