The Action of Aluminum Chloride on Ethyl-β-C¹⁴-benzene^1a,b

New Friedel-Crafts chemistry. 34. Production of branched alkanes by acid-catalyzed dealkylation of linear alkylbenzenes

“…2-Phenylpentane, 2-phenylhexane, and 3-methyl-2-phenylpentane were prepared by addition of the appropriate alkylmagnesium bromide to acetophenone, dehydration of the carbinol, and low-pressure hydrogenation of the alkene using palladium-on-charcoal catalyst in the presence of a small amount of perchloric acid. 13 3-Phenylpentane, 3-phenylhexane, and 3-methyl-2-phenylbutane were synthesized by addition of phenylmagnesium bromide to the appropriate ketone, followed by dehydration and catalytic hydrogenation. 2-and 3-Bromohexane were made from the corresponding alcohols, triphenylphosphine, bromine, and dimethylformamide.14 Authentic butanes, pentanes and hexanes were obtained from Phillips Petroleum Co.15 All of the starting materials were checked for purity by infrared spectrophotometry and GLC before use.…”

New Friedel—Crafts Chemistry. XVI.1 A Reconsideration of Cyclialkylation and Competing Reactions of Certain Phenylalkyl, Benzoylalkyl, and Acetylphenylalkyl Chlorides

“…n-CgHgCeHa (92), (C4H6)2CaH4 (8), residue (50) ra-C4HgCaH5 (77), (C4H9)2C,H4 (23), residue (41) 1.1-Dimethylindan (25), isopentylbenzene (75), residue (47) 1-Dimethylindan (38), isopentylbenzene (61), f-pentylbenzene (1), residue (32) 1.1-Dimethylindan (47), isopentylbenzene (50), i-bentylbenzene (3), residue (38) 1.1-Dimethylindan (31), isopentylbenzene (69) 1.1-Dimethylindan (100), residue (54) 1.1-Dimethylindan (4), 2-methyltetralin (33), 1-methyltetralin (ca. 1), isopentylbenzene (62), residue (27) 1.1-Dimethylindan (8), 2 methyltetralin (52), 1-methyltetralin (ca.…”

“…6), isopentylbenzene (34), residue (23) 1.1-Dimethylindan (2), 2-methyltetralin (65), 1-methyltetralin (ca. 2), isopentylbenzene (31), residue (27) 1-Methyltetralin (98), n-C6HiiCeH6 (2), residue (19) 1-Methyltetralin (99), ro-CEHnCeHE (1), residue (22) 1.1-Dimethyltetralin (35), isohexylbenzene (55), unidentified (10), residue (41) 1.1-Dimethyltetralin (25), isohexylbenzene (56), unidentified (19), residue (46) 1.1-Dimethyltetralin (100), residue (17) 2-Phenyltetralin (93), tetralin (7), 1-benzylindan (trace) 2-Phenyltetralin (15), tetralin (70), 1-benzylindan (3), unidentified (12) 2-Phenyltetralin (1), tetralin (50), unidentified (48) Unchanged starting material (100) No cyclialkylation products 3-Methyl-l-indanone (83), unidentified (17), residue (32) 5-and 6-acetyl-l-methylindan isomers in roughly equal amounts (32), pacetylbutylbenzene (12), 6-acetyltetralin (5), acetophenone (3), unidentified (48), residue (36) " Molar ratio of A1C13 or FeCl3 to phenylalkyl chloride was 0.50; AlCls was the catalyst in all experiments unless specified. 6 In all experiments, unless specified, a ratio of solvent (milliliters) to phenylalkyl chloride (grams) of ca.…”

REARRANGEMENT STUDIES WITH C14. X. ETHANOL-2-C14 FROM THE IRRADIATION OF ETHANOL-1-C 14 WITH Co60 GAMMA RAYS

“…In the present study, dilute aqueous solutions of ethanol-1-C14 was irradiated with Co60 y-rays to ascertain whether any isotope position rearrangement to ethanol-2-C14 would result. Detection of such a rearrangement could possibly be regarded as indicating some rupture of the carbonoxygen bond to give an ethyl radical followed by a 1,2-hydrogen shift in the radical analogous to 1,2-hydride shifts observed in certain reactions involving the ethyl c a t' ion (7,8,9). X stock solution containing 2.O2Y0 ethanol by weight was made up with distilled water and e t h a i~o l -l -C~~.…”