Diphenyl-2-propen-l-one

Diphenylisoxazole can be synthesized by the reaction of hydroxylamine chloride with 3-anilino-l,2-diphenyl-2-propen-l-one or formyldeoxybenzoin, PhC(CHO)=C(OH)Ph <62HC(17)1, p. 57). 

The cobalt complex 37 was used in combination with quinine as a chiral coordinating base to hydrogenate l,2-diphenyl-2-propene-l-one in 49% ee (Fig. 29.22) [50]. However, no further studies of this type of catalyst were reported. 

In the reaction of 2-cyclohexenone and of 4-phenylbut-3-en-2-one with chiral organocuprates of type (205), optical yields of only 5% and 15%, respectively, were obtained201 . Methylation of l,3-diphenyl-2-propene-l-one with (205) (R = CH3) produced (S)-l,3-diphenyl- 1-butanone in 68% enantiomeric excess 202>. 

C15H120 trans-1,3-diphenyl-2-propen-l -one 614-47-1 619.15 55.442 2 28383 C15H16 2-methyl-1,1 -diphenyl ethane 32341-92-7 562.15 49.886 1,2... 

A mixture of l,3-diphenyl-2-propen-l-one, la (0.42 g, 2 mmol) and ammonium acetate (0.16 g, 2.2 mmol) in the presence of a catalytic amount of acetic acid was stirred at 100°C for 4h (progress of the reaction followed by TLC monitoring). The reaction mixture was then cooled to room temperature and the crude solid obtained was recrystallized from absolute ethanol. The product 2 a was obtained in 91% yield as colorless crystals, mp 134-135 °C. 

The crude l,3-diphenyl-2-propen-l-one was purified by column chromatography (5% EtOAc/hexanes) followed by concentration and high-vacuum drying (0.79 g, 70% yield, as a yellowish oil).[5]... 

Other cobalt catalysts that have been used for enantioselective C—C double bond reduction of a,/ -unsaturated carbonyl compounds are vitamin B12 in combination with zinc/acetic acid (up to 33% ee)S7 and bis(dimcthylglyoximato)cobalt(II) (12) with chiral amines as cocatalysts88 and molecular hydrogen as reducing agent. The best results have been obtained with complex 12 and quinine or (2.S )-A -[(/ )-1 -phenethyl]-2-quinuclidinecarboxaniide (hydrogenation of 1,2-diphenyl-2-propen-l-one 49% ee A, /V -dimethyl-5-benzylidenehydantoin 79% ee). 

Another example is the reduction of l,3-diphenyl-2-propen-l-one (3a), a chalcone, into 1,3-diphenyl-l-propanone (4a) by a bacterium50,51. 

The Corey-Chaykovsky reaction will be used to cyclopropanate your chalcone from Experiment 61. The reaction involves the reaction of trimethylsulfoxonium iodide and potassium fcrf-butoxide in anhydrous dimethylsulfoxide (DMSO). The reaction is stirred at room temperature for 1 hr. For example, frans-chalcone (1,3-diphenyl-2-propen-l-one) produces an 88% yield of the cyclopropanated product. You will analyze your product by NMR and infrared spectroscopy. 

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