3-Phenyl- , - acyl

Imidazole, 1 -methyl-5-nitro-2-styryl-ozonolysis, 5, 437 Imidazole, l-methyl-2-phenyl- C NMR, 5, 354 Imidazole, l-methyl-4-phenyl- C NMR, 5, 355 Imidazole, 2-methyl-4-phenyl-acylation, 5, 402... 

R, Rj = alkyl, phenyl, acyl acyloxy, sulfonyl Rj= H, OH, 0-alkyl ... 

H-2,3-Benzodiazepine, 3,4-dihydro-synthesis, 7, 596, 599 5H-2,3-Benzodiazepine, 4-phenyl-acylation, 7, 602 photochemical reactions, 7, 600 5 H-2,3 - Benzodiazepine, 1,2,3,4-tetrahydro-synthesis, 7, 596... 

Bruice TC, Benkovic SJ. A comparison of the bimolecular and intramolecular nucleophilic catalysis of the hydrolysis of substituted phenyl acylates by the dimethylamino group. J Am Chem Soc 1963 85 1-8. 

The substituents with leading atom carbon are arranged in the order primary alkyl—secondary alkyl—tertiary alkyl—cyclic alkyl—vinyl—phenyl—acyl—acyloxy—cyano. 

An impressive illustration of the influence of the medium on the photo-Fries reaction product distribution can be found in Scheme 35. Remarkably, whereas in solution eight products are formed, within NaY zeolite a single product dominates the product mixture. Cations present within zeolites help to anchor the reactants, intermediates, and products to the surfaces of the zeolite and control the reactivity of the intermediates. In this case, the cation binding not only forced the phenyl acyl radical to react at the ortho-position preferentially but also prevented it from decarbonylation. 

TTie true ketones, in which the >CO group is in the side chain, the most common examples being acetophenone or methyl phenyl ketone, C HjCOCH, and benzophenone or diphenyl ketone, C HjCOC(Hj. These ketones are usually prepared by a modification of the Friedel-Crafts reaction, an aromatic hydrocarbon being treated with an acyl chloride (either aliphatic or aromatic) in the presence of aluminium chloride. Thus benzene reacts with acetyl chloride... 

Indene derivatives 264a and 264b are formed by the intramolecular reaction of 3-methyl-3-phenyl-l-butene (263a) and 3,3,3-triphenylpropylene (263b) [237]. Two phenyl groups are introduced into the /3-substituted -methylstyrene 265 to form the /3-substituted /3-diphenylmethylstyrene 267 via 266 in one step[238]. Allyl acetate reacts with benzene to give 3-phenylcinnamaldehyde (269) by acyl—O bond fission. The primary product 268 was obtained in a trace amount[239]. 

Aminothiazolium hydroxide inner salts (2) (X = NR) are only known as N-phenyl (29) or acyl derivatives. (6. 34) or as hydrochlorides (35). 

When the cyclic component is benzene or naphthalene, the -ic acid or -oic acid of the acid corresponding to the acyl group is changed to -ophenone or -onaphthone, respectively. For example, C5H5—CO—CH2CH2CH3 can be named either butyrophenone (or butanophenone) or phenyl propyl ketone. 

Fiiedel-Ciafts acylation of phenyl methyl thioethei with 3-methylbutanoyl chlotide gives 4-acetylated thioethei, which is used as an intermediate for antihypeitensive dmgs (92). 

For the sulfonamides, the best activity is found where R is heterocycHc, but it can also be isocycHc or acyl. For the sulfones, R can be phenylene or a heterocycle the parent dapsone, where R is phenyl, is the most active. 

However, this method is appHed only when esterification cannot be effected by the usual acid—alcohol reaction because of the higher cost of the anhydrides. The production of cellulose acetate (see Fibers, cellulose esters), phenyl acetate (used in acetaminophen production), and aspirin (acetylsahcyhc acid) (see Salicylic acid) are examples of the large-scale use of acetic anhydride. The speed of acylation is greatiy increased by the use of catalysts (68) such as sulfuric acid, perchloric acid, trifluoroacetic acid, phosphoms pentoxide, 2inc chloride, ferric chloride, sodium acetate, and tertiary amines, eg, 4-dimethylaminopyridine. 

When large groups, such as phenyl, bromo, ethoxycarbonyl or nitro are attached at position 3, the principal products are l-alkylcinnolin-4(l/f)-ones. Cyanoethylation and acetylation of cinnolin-4(l/f)-one takes place exclusively at N-1. Phthalazin-l(2/f)-ones give 2-substituted derivatives on alkylation and acylation. Alkylation of 4-hydroxyphthala2in-l(2/f)-one with an equimolar amount of primary halide in the presence of a base leads to 2-alkyl-4-hydroxyphthalazin-l(2/f)-one and further alkylation results in the formation of 4-alkoxy-2-alkylphthalazinone. Methylation of 4-hydroxy-2-methyl-phthalazinone with dimethyl sulfate in aqueous alkali gives a mixture of 4-methoxy-2-methylphthalazin-l(2/f)-one and 2,3-dimethylphthalazine-l,4(2//,3//)-dione, whereas methylation of 4-methoxyphthalazin-l(2/f)-one under similar conditions affords only 4-methoxy-2-methylphthalazinone. 

---