1-Naphthyl phenyl ketone

Figure 6.10. Rate constants for quenching of sensitizers by cis- and trans-stilbenes (open and filled circles, respectively). Sensitizers are as follows (1) tri-phenylene, (2) thioxanthone, (3) phenanthrene, (4) 2-acetonaphthone, (3) 1-naphthyl phenyl ketone, (6) crysene, (7) fluorenone, (8) 1,2,5,6-dibenzanthracene, (9) benzil, (10) 1,2,3,4-dibenzanthracene, (11) pyrene, (12) 1,2-benzanthracene, (13) benzanthrone, (14) 3-acetyl pyrene, (15) acridine, (16) 9,10-dimethyl-l,2-benzanthracene, (17) anthracene, (18) 3,4-benzpyrene.<57> Reprinted by permission of the American Chemical Society.

C16H30O4 hexadecanedioic acid 505-54-4 25.00 0.9397 2 29889 C17H120 2-naphthyl phenyl ketone 644-13-3 25.00 1.1506 2... 

Benz[de]anthrone 272 A finely divided mixture of 1-naphthyl phenyl ketone (1 part) and anhydrous aluminum chloride (5 parts) is heated, with protection by a calcium chloride tube, during 0.5 h from 60° to 115°, during a further 1 h from 115° to 130°, and during a final 1 h from 130° to 150°. The cake is decomposed by dilute hydrochloric acid, and the resulting solid is filtered off and washed with alcohol and ether it then consists of moderately pure benzanthrone (yield 76%). Recrystallization from glacial acetic acid, with charcoal, affords the pure compound as pale brown needles, m.p. 167-168° (uncorr.). 

Scholl reactions generally lead to six-membered rings but a few cases have been reported where five-membered rings were formed, particularly from ketones that carried a hydroxyl or an alkoxyl group para to the carbonyl group, such a case was reported by Fierz-David and Jaccard275 who found that 4-hydroxy-1-naphthyl phenyl ketone (and its methyl ether) gave 5-hydroxy-benzo[a]fluoren-l 1-one and not 4-hydroxybenz[de]anthrone ... 

If there is a substituent in the peri-position to the carbonyl group, then also a five-membered ring may be formed, as Dziewonski and Moszew277 found in the conversion of 8-benzyl-l-naphthyl phenyl ketone into l-benzylbenzo[a]-fluoren-ll-one ... 

This reaction is based on the formation of a color in a mixture of an aqueous sodium nitroprusside solution with carbonyl compounds in an alkaline medium. A positive test is obtained with aliphatic and certain aromatic aldehydes and aromatic and aliphatic ketones. The literature data on this reaction are conflicting and no general rule can be expressed about which carbonyl compounds give the reaction and which do not. For example, the color is not produced with formaldehyde, glyoxal, benzaldehyde, o-hydroxy-benzaldehyde, chloral, vanillin, benzophenone, naphthyl phenyl ketone, trihydroxybenzophenone, benzil, acetophenones substituted on the aromatic nucleus with hydroxyl, etc. The reaction can therefore be used for the differentiation of certain types of aldehydes and ketones, as, for example, acetaldehyde from formaldehyde, and acetophenone from benzophenone or hydroxyacetophenone, etc. Further, various colors formed in alkaline media or after the subsequent acidification of the reaction mixture can also be used for differentiation. Sodium hydroxide can be replaced by ammonia, piperidine... 

FIGURE 27.15 Saltiel plot for the sensitized Pre/Tachy interconversion. Photostationary Pre/Tachy ratios are given for benzophenone (1), anthraquinone (2), 2-naphthyl phenyl ketone (3), henzil (4), fluorenone (5), and benzanthrone (6) for the vitamin D2 system, 2 (6-hydroxy-3-oxo-3H thioxanthene-9-yl)henzene-sulphonic add (7) and 7,12-dimethylbenzanthracene (8), for the vitamin D, system, and anthracene (9) for both vitamin D2 and D, systems. ... 

A remarkably high diastereoselective excess was obtained in the addition of the anion of (S)-(-)-methyl 1-naphthyl sulfoxide to n-alkyl phenyl ketones. The sulfoxide was prepared in optically pure form by oxidation of the complex of methyl 1-naphthyl sulfide and 13-cyclodextrin with peracetic acid followed by crystallization. Desulfurization of the adducts provided enantiomerically pure tertiary alcohols (393]. 

Inasmuch as naphthyl ketones are not totally unreactive at hydrogen abstractions 54,60), there must be a small amount of reactivity intrinsic to n,n states. Such reactivity is actually known for 71,71 olefin triplets 81> and for enone triplets 6 2). In the case of phenyl ketones the carbonyl and aryl jr-systems are mixed, such that a locally excited carbonyl n,n triplet contributes a small fraction to the overall wave function for the triplet. Given this intrinsic reactivity, which is some 10-4—10-6 that of an n,n triplet, the observed reactivity of 71,71 triplets with nearby n,7t triplets can be expressed as follows, where k% is the rate constant... 

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