Sodium amide, also

Reaction with sodium amide also yields the same compound with liberation of ammonia ... 

Dehydrohalogenation with sodium amide also provides a useful method for closing an aziridine ring, as illustrated by the preparation of N-ethylallenimine (I -ethyl-2-methylenaziridine). ... 

This reaction also occurs slowly when sodium is dissolved in liquid ammonia initially a deep blue solution is formed which then decomposes giving hydrogen and sodium amide. 

Water can also be a Brpnsted acid donating a proton to a base Sodium amide (NaNH2) for example is a source of the strongly basic amide ion which reacts with water to give ammonia... 

Nucleophilic aromatic substitution can also occur by an elimination-addition mechanism This pathway is followed when the nucleophile is an exceptionally strong base such as amide ion m the form of sodium amide (NaNH2) or potassium amide (KNH2) Benzyne and related arynes are intermediates m nucleophilic aromatic substitutions that pro ceed by the elimination-addition mechanism... 

Hydrazinium salts, N2H5 X, are acids in anhydrous hydrazine, metallic hydrazides, N2H, are bases. Neutralization in this solvent system involves the hydrazinium and hydrazide ions and is the reverse of equation 7. Metal hydrazides, formally analogous to the metal amides, are prepared from anhydrous hydrazine and the metals as well as from metal amides, alkyls, or hydrides. (The term hydrazide is also used for organic compounds where the carboxyUc acid OH is substituted with a N2H2.) Sodium hydrazide [13598-47-5] is made from sodium or, more safely, from sodium amide (14) ... 

Sodium hydride, sodium amide, or other strong bases also can be used. The reagent can be generated in the presence of an appropriate carbonyl compound that reacts direcdy. 

The ring opening of 3-substituted isoxazoles proceeds differently, and the reaction can take various courses depending on the nature of the substituent. The reaction has been effected by sodium hydroxide and sodium ethoxide in alcoholic or aqueous media and by sodium amide and also n-butyllithium in inert solvents. 

To cleave the isoxazole ring, good results were also obtained by using other alcoholates as well as the recently suggested sodium amide, The latter is, however, hardly to be recommended as a general reagent. 

An a ,/3-epoxycarboxylic ester (also called glycidic ester) 3 is formed upon reaction of a a-halo ester 2 with an aldehyde or ketone 1 in the presence of a base such as sodium ethoxide or sodium amide. Mechanistically it is a Knoevenagel-type reaction of the aldehyde or ketone 1 with the deprotonated a-halo ester to the a-halo alkoxide 4, followed by an intramolecular nucleophilic substitution reaction to give the epoxide 3 ... 

Butylation of ethyl phenylacetate, /-butyl phenylacetate, and ethyl 2-phenylhexanoate has also been accomplished with M-butyl bromide and sodium hydride in refluxing monoglyme in 64%, 66%, and 56% yields, respectively.6 In contrast to the sodium amide reactions above, however, careful fractionation of the crude products was required to obtain pure products. 

Carboxylic esters can be treated with ketones to give p-diketones in a reaction that is essentially the same as 10-118. The reaction is so similar that it is sometimes also called the Claisen condensation, though this usage is unfortunate. A fairly strong base, such as sodium amide or sodium hydride, is required. Yields can be increased by the catalytic addition of crown ethers. Esters of formic acid (R H) give P-keto aldehydes. Ethyl carbonate gives P-keto esters. 

The overall sequence of three steps may be called the Wittig reaction, or only the final step. Phosphonium salts are also prepared by addition of phosphines to Michael alkenes (hke 15-8) and in other ways. The phosphonium salts are most often converted to the ylids by treatment with a strong base such as butyllithium, sodium amide, sodium hydride, or a sodium alkoxide, though weaker bases can be used if... 

See Hyponitrous acid, also Sodium amide (reference 4)... 

This is a general method for making N-alkylallenimines, and the following ones have been made in this way N-methyl-,6 N-propyl-,6 N-isopropyl-,4 N-butyl-,4 N-hexyl-,e and N-(3,5,5-tri-methylhexyl)-.4 N-Z-Butylallenimine6 and l-(l-allenimino)-2-hydroxy-3-butene 7 have also been prepared by this method, but with sodium amide/2-bromoallylamine mole ratios of 1.75 and 2.1, respectively. This method has been used for the preparation of pure N-alkylpropargylamines from 2-chloroallylaminesA7 The optimum sodium amide/2-chloroallylamine ratio for the preparation of N-alkylpropargylamines is 2.1. 

This preparation may be accomplished by using one molecular equivalent of lithium amide special reaction procedures must be employed, however, and the yields are not reproducible.2 The preparation may also be accomplished (with reduced yield) by using sodium amide, but only under special reaction conditions.3... 

One should not pour the liquified ammonia directly out of the cylinder since particles of iron compounds might be carried along, catalyzing the formation of sodium amide. For the exclusion of moisture it is also necessary to use a drying tower (potassium hydroxide) between the cylinder and the flask. 

As far as propargyl thioethers are concerned, the substrates in this section follow all the principles discussed for propargyl ethers and propargylamines in the two preceding sections. For alkyl propargyl thioethers typical bases used are sodium amide in liquid ammonia, alcoholate or alkali metal hydroxide [178, 186-189, 191, 287-291], and again some derivatives of carbohydrates have been used successfully [292, 293], If an ester group is also present in the molecule, the reaction can be accompanied by a hydrolysis to the carboxylate [294]. 

After the first attempts of a Russian school to prepare 6 [1], Ball and Landor [4] also did not arrive at a conclusive result when they treated 1-chlorocyclohexene (32a) with sodium amide. Wittig and Fritze [50] were the first to demonstrate clearly the existence of 6. After the reaction of 1-bromocyclohexene (32b) (Scheme 6.9) with potassium iert-butoxidc (KOtBu) in dimethyl sulfoxide (DMSO), they isolated the dimer 38 (Scheme 6.10) of 6 in 7% yield and, when the elimination was performed... 

Caubere et al. [64, 65] also employed enolates as nucleophiles to intercept the intermediates produced from 32a and the mixture of sodium amide and a sodium enolate. Scheme 6.12 illustrates the results obtained by using the enolates of cyclohexanone and cyclopropyl methyl ketone. The former furnished only the ketone 43 in hexamethylphosphoric triamide as solvent, but almost exclusively the cyclobuta-... 

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