2-Nitrocarboxylic acids

The hrst step (1) gives rise to nitrocarboxylic acid esters (37) (If R=X=H, special conditions are required to prevent the double addition of the Michael substrate to reagents (36)). 

Cunico and Motta reported (202) on the very interesting one-pot synthesis of SENAs, such as 3-nitrocarboxylic acid /V./V-dimethylamides derivatives, from silylated N./V-dimethylformamides 57a,b and conjugated nitroalkenes (Scheme 3.57). 

Treating the dianion of a carboxylic acid with an alkyl nitrate leads to an a-nitrocarboxylic acid which readily undergoes decarboxylation to the corresponding nitroalkane. This method is particularly useful for the synthesis of arylnitromethanes containing electron-donating groups. ... 

Nitrocarboxylic acids Nitrodiazome thanes Nitro derivatives of urea N,/V-bis(, p, )-t initrocthyl urea Nitroso compounds... 

Other stabilized anions that were successfully C-arylated include the anions of nitroalkanes, a-methyl-a-nitrocarboxylic acid derivatives, esters, triphenylmethane, indole and scatole. Nitroalkanes gave high yields of the a-C-aryl derivatives. Ita the presence of BTMG, 2-nitropropane reacts with triphenylbismuth dichloride or tetraphenylbismuthonium p-toluenesulfonate to lead to a-nitrocumene (86 or 77% respectively). The reaction using triphenylbismuth dichloride and TMG was applied to the synthesis of a-methyl-a-phenylglycine via arylation of a-nitropropionic acid esters. ... 

Reactions of carbonyl compounds with nitroalkanes like nitromethane (Henry reaction) are described in Volume 2, Chapter 1.10. The doubly activated ethyl nitroacetate readily reacts with aliphatic, aromatic and heteroaromatic aldehydes to give a,p-unsaturated-a-nitrocarboxylic acid esters in the presence of TiCU/V-methylmorpholine as mixtures of cis and trans isomers. ... 

Reaction of levoglucosenone with amides of a-nitrocarboxylic acids resulted in the formation of the tetrahydropyridones 77 and with acetoacetic acid amides, mixtures of the keto and enol tautomers were obtained [137]. 

Lithium tetrahydridoaluminate sulfuric acid Diamines from nitrocarboxylic acid amides... 

Cyclic hydroxamic acids from nitrocarboxylic acid esters O... 

N-Benzoyl-N-methylnitrosamine added to a stirred suspension of 2 eqs. ethyl mercaptan and 1.5 eqs. NaH in dry tetrahydrofuran at room temp, in the presence of 4A molecular sieves, and stirred for 20 min S-ethyl-thiobenzoate. Y 95%. F.e. inch S-aryl thiolates, also (more rapidly) from N-nitrocarboxylic acid amides, s. R. Beren-guer et al.. Synthesis 1989, 305-6. 

Excellent yields have been reported for a transformation consisting of the reaction of 2-nitrocarboxylic acids, and derivatives thereof, with formamide or A -methylformamide in the presence of indium(III) or bismuth (III) salts. ... 

Sulfuric acid/sodium nitrate Nitrocarboxylic acid amides from nitriles... 

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