5810-22-0Relevant academic research and scientific papers
Transformations of peroxide products of olefin ozonolysis in tetrahydrofuran in reactions with hydroxylamine and semicarbazide hydrochlorides
Ishmuratov,Legostaeva,Garifullina,Botsman,Muslukhov,Ishmuratova,Tolstikov
, p. 928 - 933 (2014/10/15)
Treatment with hydroxylamine and semicarbazide hydrochlorides of peroxide products obtained by ozonolysis of olefins in tetrahydrofuran gives mainly carboxylic acids and their derivatives.
Selective hydrolysis of aliphatic dinitriles to monocarboxylic acids by a nitrilase from Arabidopsis thaliana
Effenberger,Osswald
, p. 1866 - 1872 (2007/10/03)
The hydrolysis of a variety of dinitriles including α,ω-dicyanoalkanes 1, β-substituted glutaronitriles 5, and γ-cyanopimelonitrile 7 with a recombinant plant nitrilase from Arabidopsis thaliana, expressed in E. coli, is described. Conversion rate and selectivity of the hydrolysis of dinitriles 1a-f to ω-cyanocarboxylic acids 2a-f depend on the chain length. The enzyme activity markedly increases from malononitrile (1a) to octanedinitrile (1f). The selectivity, however, does not correlate with the rates. Up to a chain length of 6 C-atoms, the cyanocarboxylic acid is the only product, even at complete conversion of the starting material. Pimelonitrile (1e) is hydrolyzed to the cyanocarboxylic acid 2e without formation of diacid (1%) up to 73% conversion. Glutaronitriles 5a-c were also hydrolyzed to the corresponding cyanobutanoic acids 6a-c with perfect selectivity. The nitrilase hydrolyzes exclusively the primary cyano group of 7 to give 3,5-dicyanoheptanoic acid (8a), whereby the selectivity is slightly reduced compared to the unsubstituted pimelonitrile (1e). If the hydrolysis is terminated at conversions ≤90%, pure 8a can be isolated in 72% yield (92% referred to conversion). After esterification of 8a to the methyl ester 8b, only the 5-cyano group but not the ester function was hydrolyzed enzymatically to give cyanoheptanedioic acid monoester (10).
