Action of Aromatic Alcohols on Aromatic Compounds in the Presence of Aluminum Chloride. I.

Abstract

a crystal of the substance added, the thiourethane separates in thin prismatic plates. It melts a t 37' apparently undecomposed.

The acid-mediated ring opening reactions of α-aryl-lactams

“…1 Acid-mediated displacement of aryls by benzene is also known to occur in the isolation of diphenylmethane from the alkylation of benzene by substituted arylmethanols 8 and substituted benzyl halides. [9][10][11][12][13][14] In addition, there are two reports of acid-mediated aryl-benzene exchange with diarylmethanes. 8,9 Next we explored the reactions of other substituted azetidinones.…”

Friedel-Crafts Reactions

“…Illari (12), in continuing his investigations on the mechanism of Friedel-Crafts reactions, refers to prior reports of Norris and Sturgis (27) on the condensation of aliphatic alcohols: C2H5OH + AlCb -> C2H50H.A1C13 -> C2H50A1C12 + HCI -> C2H5CI + AlOHCh C2H3OH ~T" CfiHe -j-AICI3-> C211. '.C' 11 ,¡ -j-HCI -AlOHCL as well as to the papers of Huston and Friedemann (10,11) pertaining to the condensation of benzyl alcohol: above 40°C.…”

Trifluoroacetic Acid-Promoted Friedel-Crafts Aromatic Alkylation with Benzyl Alcohols

“…White solid (mixture from EtOH); Yield 68%; mp 58-64 °C (Lit [38], for 20, mp 85-86 °C; for 21, mp 78 °C); NMR (CDCl 3 ) δ 7.7-7.0 (m, 28H), 4.45 (s, 4H), 3.90 (s, 4H); the latter peaks in a 3:1 ratio; (Lit [39], (for 20) NMR (CDCl 3 ) δ 7.30 (m, 4H), 7.23 (m, 6H), 7.16 (m, 4H), 3.99 (s, 4H); GC also showed two peaks in a ratio of 3:1. The major isomer (20) agreed by comparison with an authentic sample as prepared below.…”

“…The mixture was refluxed for 24 h. The usual workup afforded an oil (2.23 g) that solidified. Crystallization from EtOH gave colorless crystals (0.439 g in two crops) of 20, mp 84-85 °C (Lit [38], mp 85-86 °C). This material was identical to the major isomer 20 as prepared above from diphenylmethane.…”