THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS¹

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

“…The bromination of ketones with bromine is a reversible process. In order to shift the equilibrium towards the bromoketones, preparations have to be proceeded with removal of hydrogen bromide [ 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 ].…”

The Chemistry of α‐Haloketones and Their Utility in Heterocyclic Synthesis

“…The bromination of ketones with bromine is a reversible process. In order to shift the equilibrium towards the bromoketones, preparations have to be proceeded with removal of hydrogen bromide [63][64][65][66][67][68][69][70][71][72][73][74][75].…”

The Anodic Oxidation of 1,1-Diphenyl Ketones in the Presence of Nucleophiles

“…Compound B (RT = 5.5 minutes) was identified as cyclohexyl acetate ( 22) based on comparison of its retention time and fragmentation pattern to those of a synthetic sample 21 , prepared from the reaction of cyclohexanol with acetic anhydride in the presence of catalytic ptoluenesulfonic acid. synthetic sample and those in the literature 22 , prepared by the reaction of benzhydryl chloride (24) with acetic acid. = 350.…”

“…based on comparison of its retention time and fragmentation pattern to those of a synthetic sample. This new compound was synthesized by the sequential bromination of 1,1-diphenylacetone (18) according to a literature procedure 24 followed by reaction of the product from this reaction, 1-bromo-1,1-diphenylacetone ( 26 23. The above figure shows the mass spectrum obtained for this compound.…”

“…To a 100 mL round-bottom flask containing 30 mL THF and a stir bar was added 0.195 g (1.00 x 10 -3 mol) of silver tetrafluoroborate and 0.097 g (8.930 x 10 -4 mol, 0.0925 mL) of benzyl alcohol. To this solution was added 0.182 g (9.00 x 10 -4 mol, 0.160 mL) of benzhydryl chloride (24), with the solution rapidly turning an opaque white color. The reaction was allowed to stir for thirty minutes, after which time was added 0.094 g (1.075 x 10 -3 mol) of sodium bicarbonate.…”