Propiophenone 3,3-diphenyl

Propiophenone. Prepare a solution of diphenyl-cadmium in 110 ml. of dry benzene using 4 9 g. of magnesium, 32 4 g. of bromobenzene and 19 5 g. of anhydrous cadmium chloride. Cool the solution to 10°, and add during 3 minutes a solution of 14 -8 g. of propionyl chloride (b.p. 78-79°) in 30 ml. of dry benzene use external coohng with an ice bath to prevent the temperature from rising above 40°. Stir the mixture for 2 hours at 25-35°. Work up the product as detailed above except that 6 per cent, sodium carbonate solution should replace the saturated sodium bicarbonate solution. The yield of propiophenone, b.p. 100-102°/16 mm., is 17 6 g. 

Photoinitiators 2-hydroxy-2-methyl propiophenone and diphenyl-(2,4,6-trimethylbenzoyl) phosphine oxide both gave at least 100 MEKDR with no damage to the film surface when cured at a dosage as low as 0.5 J/cm2. This preference in photoinitiators has been observed in other studies of the maleate/vinyl ether system.1011... 

Propanol with magnesium in reduction of chlorobenzene, 47, 104 Propionic acid, 2-(2,4,5,7-tetranitro-flcoken-9-ylideneamtnooxv)-, (+)- AND (-)-, 48, 120 Propionyl fluoride, 45, 6 Propiophenone, condensation with paraformaldehyde, 48, 91 -Propylaminc, 45, 85 -Propylhydrazine, 45, 85 C-( -Propyl)-N-phenylnitrone, generation from phenylhydroxylamine and -butyraIdehyde, 46, 97 Purification of tetrahydrofuran (Warning), 46,105 477- Pyran-4-0ne, 2-6-dimethyl-3,5-DIPHENYL-, 47, 54... 

Deamination of amines often gives rise to hot, short-lived carbocations (Section 5.2, p. 226). Deamination of ( + )-1,1-diphenyl-2-amino-l-propanol specifically labeled with 14C in one of the two phenyl groups (25) gives a-phenyl-propiophenone as product, 88 percent of it inverted and 12 percent retained. All the inverted ketone comes from migration of the 14C-labeled phenyl and all the retained from migration of the unlabeled phenyl group (Equation 6.22).39 This... 

The reaction is illustrated by the formation of propiophenone from diphenyl-cadmium and propanoyl chloride (Expt 6.126). Better yields are obtained by carrying out the synthesis in this manner rather than attempting the alternative combination of diethylcadmium with benzoyl chloride. Alternatively an alkyl-lithium cuprate could be used with an aromatic acid chloride (p. 616). 

Diphenyl-2,3,4,5-tetrahydropyridazine (XLIX) is structurally similar to a benzyl-hydrazone of propiophenone, and accordingly, a four-eletron polarographic wave is observed in acid solution with formation of L [306]. The electrode reaction is as follows ... 

S,3R)-4-Dimethy]amino-3-methyI-l,2-diphenyl-2-butanol (7) is a commercially available compound which is produced on an industrial scale because of the analgesic effects of its esters6. It has also been called dextrocarbinol base, or Darvon alcohol, or Chirald. It can be prepared from propiophenone by Mannich reaction with subsequent addition of benzylmagnesium chloride6. Resolution is achieved with ( — )-10-camphorsulfonic acid. Applications include enantioselective reduction of ketones by complex hydrides modified with this amino alcohol8,9 and catalysis in the addition of zinc alkyls to carbonyl compounds (Section D. 1.3.1.4.). 

For example, reaction of propiophenone and benzonitrile with mercury(ll) tosylate affords 2,4-diphenyl-5-methyloxazole 196 (Scheme 1.52). Mechanistically, the authors proposed initial formation of a di(a-arylalkanoyl)Hg(ll) species 192 from reaction of the enol tautomer of propiophenone with mercury(II) tosylate. Reaction of 192 with benzonitrile generates 193, which collapses to the oxirane 194 with loss of mercury. Rearrangement of 194 and loss of... 

Ai)i]iilB. / -diphenyl-propiophenon 14 125. 9 PhenyI 9-[4-dimethyla nmo-phenyi]o xanthen 18, 589. 

Phenyl- 9,p,tolyl-propiophenon 7 II488. a.a-Dlpnen -a-oenzyl-aceton 7 II483. aj.a>-ra-p-tolyl-aoetophenon 7 II489. aj-Athyi4U,(U-diphenyl-aceiophenon 7 1 295. Athyl-trlphenylmethyl-keton 7 I 295. 3 -Methyl-5. 6. 7. 8 -tetrahydro-1.2 -dinaph< thylketon 7 II489. 

Aromatic ketones are often named by treating the benzene ring as a phenyl group, as in isopropyl phenyl ketone (Fig. 16.12). A few can be named through the lUPAC system in which the framework Ph—C=0 is indicated by the term ophenone and the remainder of the molecule designated by one of the alternative names in Rgure 16.12. Thus, diphenyl ketone is benzophenone, methyl phenyl ketone is acetophenone, ethyl phenyl ketone is propiophenone, and phenyl propyl ketone is butyrophenone (Fig. 16.12). 

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