Alkylation of Benzene with Cyclopropane‐Containing Polycyclic Hydrocarbons under the Action of the [Et₃NH]⁺[Al₂Cl₇]^– Ionic Liquid

Abstract

Benzene alkylation with cyclopropane‐containing polycyclic hydrocarbons (tetracyclo[4.3.0.02,4.03,7]nonane, exo‐exo‐hexacyclo[9.2.1.02,1003,804,605,9]‐tetradecane, exo‐endo‐hexacyclo[9.2.1.02,1003,804,605,9]tetradecane, endo‐exo‐hexacyclo[9.2.1.02,1003,804,605,9]tetradecane, and endo‐endo‐hexacyclo[9.2.1.02,1003,804,605,9]tetradecane) was accomplished under the action of the [Et3NH]+[Al2Cl7]‐ ionic liquid.

Four Stereoisomeric Norbornadiene Dimers Containing a Cyclopropane Ring: ROMP, Polymer Properties, and Post-Polymerization Modification

“…The aromatic electrophilic substitution of the four H-NBDD isomers using an ionic liquid has been reported . We also examined the model reaction of exo-exo -H-NBDD by TfOH with benzene as both reactant and solvent (entry 3 in Table ).…”

“…Therefore, we herein performed the synthesis and ROMPs of all four stereoisomers of these NBDDs. The resulting hydrogenated polymer was then subjected to PPM involving the ring-opening of the cyclopropyl moiety − to introduce different functional groups. The physical properties of all of the obtained polymers were revealed by thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), and powder X-ray diffraction (XRD) measurements.…”

Reactions of exo-exo-hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradecane with Aliphatic Alcohols under the Action of Ionic Liquids

“…The 1 H and 13 C NMR spectra were recorded on a Bruker Avance-II 400 Ascend instrument (400 MHz for the 1 H and 100 MHz for the 13 C in CDCl 3 ) and a Bruker Avance-III HD 500 Ascend instrument (500 MHz for the 1 H and 125 MHz for the 13 C in CDCl 3 ).…”

“…Colorless oil, yield 88%; 1 H NMR (400 MHz, CDCl 3 ) δ 1.21-1.25 (m, 1H), 1.26-1.28 (m, 1H), 1.35-1.39 (m, 2H), 1.40-1.43 (m, 4H), 1.48-1.53 (m, 4H), 1.71-1.76 (m, 1H), 1.86-1.90 (m, 2H), 2.09-2.15 (m, 2H), 2.82 (d, 1H, J = 4.4 Hz), 3.30 (s, 3H), 3.69-3.71 (m, 1H). 13…”

“…Ionic liquids (ILs) meet these requirements. For example, ILs based on aluminum, iron, and other metal halides are an alternative to traditional catalysts; in particular, they catalyze the Friedel-Crafts alkylation and the acylation reactions, hydrogenation, and isomerization of alkanes and polycyclic hydrocarbons [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16].…”