Succinic acid nitril

A classical way to achieve regioselectivity in an (a -i- d -reaction is to start with a-carbanions of carboxylic acid derivatives and electrophilic ketones. Most successful are condensations with 1,3-dicarbonyl carbanions, e.g. with malonic acid derivatives, since they can be produced at low pH, where ketones do not enolize. Succinic acid derivatives can also be de-protonated and added to ketones (Stobbe condensation). In the first example given below a Dieckmann condensation on a nitrile follows a Stobbe condensation, and selectivity is dictated by the tricyclic educt neither the nitrile group nor the ketone is enolizable (W.S. Johnson, 1945, 1947). 

Formal oxidation of pyrrolidine to the succinimide stage affords a series of compounds used as anticonvulsant agents for treatment of seizures in petit mal epilepsy. Knoevnagel condensation of benzaldehyde with ethyl cyanoacetate affords the unsaturated ester, 9. Conjugate addition of cyanide ion leads to the di-nitrile ester (10). Hydrolysis in mineral acid affords the succinic acid (11), presumably by decarboxylation of the intermediate tricarboxyllie acid. Lactamization with methylamine gives phensuximide (12). ... 

The first enzymatic reaction investigated in the whole project concerned the introduction of chirality in route B (Fig. 2) by generation of succinic acid mononitrile (R)-12 from its racemic precursor. Since in a broad sense the nitrile ester substrate 10 can be interpreted as an amino acid analogue, proteases recommended themselves as catalysts to be tested. From the literature, 2-substituted succinic and butyric acid esters were known to be resolved by proteases [6, 7]. Proteases are... 

Gerhardt s criterion of dibasic (and polybasic) acids is that these yield two (or more) esters of which one (or more) is acid and one is neutral. Monobasic acids form only one amide, one nitrile and one anilide, whilst the acid ammonium salts of dibasic acids (e.g. succinic) by loss of water can form also an amide-acid and a nitrile, and only the dibasic acids give anilide-acids. Salts and esters of succinic acid were investigated by F. Darcet, who discovered succinic anhydride, succinamide and succinimide, and all were again investigated by Fehling. ... 

Hydrogen peroxide nitric acid o,a-Disubst. succinic acids from nitriles... 

Reaction XLVm. (a) Action of Alkali Cyanides on Alkyl and Acyl Halides. (Bl., [2], 50, 214.)—This reaction is capable of very wide application, all the simple alkyl halogen compounds, the acyl halides, and the halogen fatty acids come within its scope. The nitriles so formed yield acids by hydrolysis, so it is frequently the first step in the synthesis of an acid—the preparation and hydrolysis of the nitrile are often combined. The preparations of malonic, succinic, tricarballylic and other acids (Preparations 60, 61, 62) illustrate this. The extension of this reaction to acyl halides is important, and should be referred to, as should the interaction of silver cyanide, and alkyl iodides, to give isonitriles. Mercuric and silver cyanides, it may be noted, give with acyl chlorides and bromides better yields of normal acyl nitriles than do the alkali cyanides. 

The most useful procedure utilises a 1,4-keto-ester giving a dihydro-pyridazinone, which can be easily dehydrogenated to the fully aromatic heterocycle, often by C-bromination then dehydrobromination alternatively, simple air oxidation can often suffice. 6-Aryl-pyridazin-3-ones have been produced by this route in a number of ways using an a-amino nitrile as a masked ketone in the four-carbon component, or by reaction of an acetophenone with glyoxylic acid and then hydrazine. Friedel-Crafts acylation using succinic anhydride is an alternative route to 1,4-keto-acids, reaction with hydrazine giving 6-aryl-pyridazinones. Alkylation of an enamine with a phenacyl bromide prodnces 1-aryl-l,4-diketones, allowing synthesis of 3-aryl-pyridazines. ... 

Laureth Laureth-9 phosphate Laurie acid Laurylpyridinium chloride Lysolecithin Magnesium dodecylbenzene sulfonate 4-(1-Methylethyl) cyclohexadiene-1-ethanol formate Myristalkonium chloride 2-Naphthalenesulfonic acid Naphthenic acid Nonoxynol-14 Nonoxynol-16 Nonoxynol-17 Nonoxynol-18 Nonoxynol-23 Nonoxynol-25 Nonoxynol-55 Nonoxynol-75 Nonoxynol-150 Nonoxynol-10 carboxylic acid Nonoxynol-3 phosphate Octadecene nitrile Octadecenyl succinic anhydride Octoxynol-4 Octoxynol-7... 

In general, esters, acid chlorides, and anhydrides are most reactive toward the Kulinkovich reagent. Carbonates and thioesters are of moderate reactivity, whereas carbonamides are least reactive. Case in point was made by chemoselective Kulinkovich reaction of succinic ester-amide 12. Cha observed that only the ester portion underwent the Kulinkovich reaction to afford cyclopropanol 13. Szymoniak demonstarted that nitriles are more reactive than ester and amides. 

Nitrile-. CgH OgN. MW, 141. Cryst. from CHCI3. M.p. 86-8°. Sol. most org. solvents, KOH —succinic and acetic acids, HCl —> levulinic acid. 

The behavior, in which two liquid phases exist in equilibrium, although hitherto not described for the hydro-carbon-oxygen systems, is not peculiar to them. The ozone-oxygen system, shown in Figure 10, has been found to exhibit such a phenomenon , and also such diverse systems as benzoic acid-water, shown in Figure 11, phenol-water, succinic nitrile-water9, zinc-bismuth, and resorcinol-water. ... 

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