Synthesis of acetic acid N-substituted amides and oligomerization of ethylene during its reaction with mercuric acetate in an amine medium

1974 ◽  
Vol 23 (10) ◽  
pp. 2288-2289
Author(s):  
B. K. Nefedov ◽  
N. S. Sergeeva ◽  
Ya. T. �idus
Keyword(s):  
Acetic Acid ◽  
Mercuric Acetate

SOME OXIDATION REACTIONS OF DELCOSINE

1957 ◽  
Vol 35 (4) ◽  
pp. 397-408 ◽  
Author(s):  
Ragini Anet ◽  
D. W. Clayton ◽  
Léo Marion
Keyword(s):  
Acetic Acid ◽  
Silver Oxide ◽  
Chromic Acid ◽  
Mercuric Acetate ◽  
Membered Ring ◽  
Oxidation Reactions ◽  
Ethyl Group ◽  
Compound C ◽  
Ring Oxidation ◽  
Group B

The alkaloid delcosine was oxidized by chromic acid in acetic acid, and also by the Oppenauer reaction, to dehydrodelcosine in which the carbonyl was shown by infrared absorption to be in a pentatomic ring. Oxidation of the alkaloid with silver oxide gave two products: (a) N-desethyldelcosine, which could be N-acetylated or converted back to the original base by ethylation, thus proving the presence of an N-ethyl group; (b) a compound, C24H37O7N, the properties of which agreed best with those of an internal ether, i.e., anhydrohydroxydelcosine. The action of N-bromosuccinimide on the alkaloid produced the same two compounds as silver oxide, plus a derivative, C22H33O7N, that proved to be N-desethyl-anhydrohydroxydelcosine. Potassium permanganate oxidized delcosine to a product, C22H31O7N, that had lost the N-ethyl group, contained the internal ether, and also a carbonyl in a five-membered ring. This same product was obtained on similar oxidation of N-desethyl-anhydrohydroxydelcosine. Oxidation of delcosine with mercuric acetate gave N-desethyldelcosine and N-desethyl-anhydrohydroxydelcosine, together with a compound that was very soluble in water and proved to be the carbinolamine formed by hydroxylation of the methylene in the N-ethyl group. These results are discussed in terms of a structure that is tentatively advanced for delcosine.

Organomercury Compounds. XXVII. The Synthesis and Properties of Some Carboxylato- and Carboxy-pyridinylmercurials

1985 ◽  
Vol 38 (3) ◽  
pp. 419 ◽  
Author(s):  
GB Deacon ◽  
GN Stretton
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Dimethyl Sulfoxide ◽  
Mercuric Acetate ◽  
Major Product ◽  
Aqueous Acetic Acid ◽  
Halide Ions ◽  
Iodide Ions ◽  
Organomercury Compounds

Decarboxylation of mercuric pyridine-2,3-dicarboxylate in hot dimethyl sulfoxide or hexamethylphosphoramide gives a mixture of 2-carboxylatopyridin-3-ylmercury(II) (major product) and 3- carboxylatopyridin-2-ylmercury(II) (minor product). The mixture reacts ( i ) with acidified halide ions ( Cl - or I-) to yield a mixture of the corresponding carboxypyridinyl ( halogeno )mercury(II) derivatives, (ii) with tribromide ions to give the bromo ( carboxypyridinyl )mercury(ii) complexes, 3-bromopyridine-2-carboxylic acid, and 2-bromopyridine-3- carboxylic acid, and (iii) with iodide ions in hot aqueous acetic acid to yield bis (2-carboxypyridin-3-yl)mercury(II) hydrogen triiodomercurate (II). Solutions of the last compound in dimethyl sulfoxide deposit bis (2-carboxypyridin-3-yl)mercury(II). Reaction of pyridine-2,3-dicarboxylate ions with mercuric acetate in boiling aqueous acetic acid at pH 5.0-5.8 gives mercurated acetic acid as the sole organometallic product, and the reported1 decarboxylation yielding 3-carboxylatopyridin-2-ylmercury(II) is not observed.

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