Studies in Stereochemistry. II. The Preparation and Complete Resolution of 3-Phenyl-2-pentanol and 2-Phenyl-3-pentanol

Molecular Rearrangements. I. The 1,2,2-Triphenylethyl System1

“…Acetic anhydride (0.5 ml.) was added, then ^-toluenesulfonic acid hydrate (0.88 g., 4.65 mmoles). The solution was heated for one hour on the steam bath, a little water was added, and crystallization was allowed to proceed.…”

“…were dissolved in warm acetic acid (21 ml.). l-Acetoxy-l,2,2-triphenylethane-l-C14 (1.46 g., 4.62 mmoles; radioactivity assay, 2.708 me./ mole) was added, and the solution was heated on the steambath for one hour. The acetate was re-isolated and deacetylated and the carbinol, 1.34 g., m.p.…”

Unlocking the Friedel-Crafts arylation of primary aliphatic alcohols and epoxides driven by hexafluoroisopropanol

“…Indeed, the association of Lewis or Brønsted acid catalysts with HFIP is known to trigger transformations with rather unreactive alcohols, alkenes, and cyclopropanes through the formation of highly reactive hydrogen-bond networks. [55][56][57][58][59][60] Under these reaction conditions, the ring-opening Friedel-Crafts reaction of most epoxides is found to be stereospecific, and the resulting alcohols can react in a second Friedel-Crafts reaction through the intermediacy of a well-established [61][62][63][64][65][66][67][68][69] but underexploited [70][71][72][73][74][75][76][77][78] phenonium ion without pre-activation of the alcohol. Simple aliphatic alcohols can also undergo a Friedel-Crafts reaction through a rare intermolecular S N 2-type mechanism, as supported by density functional theory (DFT) calculations.…”

Formation of synthetically relevant CF3-substituted phenonium ions in superacid media

“…Since the pioneering studies of Cram 1 ( Fig. 1a ), considerable interest has been focused on phenonium ions.…”