Stereospecific addition of H to fumaric acid in irradiated single crystals of succinic acid was written by Miyagawa, Ichiro;Itoh, Koichi. And the article was included in Nature (London, United Kingdom) in 1966.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:
Mixtures of succinic acid and fumaric acid grown in both aqueous solution and in heavy H2O were irradiated. In crystals grown from aqueous solution, only the primary species (DO2CCH灏?/sub>H灏?.CH浼?/sub>CO2D) was detected. In the D-substituted crystal, which contained more than 0.0001 mole fraction of fumaric acid, the the DO2CCD灏?/sub>H灏?CHCO2D species was detected in addition to the primary species. When 2,3-dideuterofumaric acid was used, the absorption from DO2CCD2CDCO2D replaced this absorption. Thus, it was concluded that the radical DO2CCD灏?/sub>H灏?CHCO2D was formed by the addition of H (deuterium) to fumaric acid. The concentration of DO2CCD灏?/sub>H灏?CHCO2D increased with increasing concentration of fumaric acid in the crystal until the latter concentration became about 0.01 mole fraction. For the crystal in which the concentration of fumaric acid was higher than 0.01, the ratio [DO2CCD灏?/sub>H灏?CHCO2D]/[DO2CCH2CHCO2D] was found to be about 0.65. From the signal-to-noise ratio of the absorption pattern of the crystal, the ratio [DO2CCH灏?/sub>D灏?CHCO2D)]/[DO2CCD灏?/sub>H灏?CHCO2D] was found to be less than 1:300. Fumaric acid was the only compound from which a radical was formed with the use of an irradiated crystal of succinic acid. The other compounds examined (inactive compounds), which are more or less similar to fumaric acid in structure, were maleic acid, oxalic acid, crotonic acid, acrylic acid, tartaric acid and (鍗?-aspartic acid. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).
4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115閳?25 ppm whereas in isonitriles the shifts are around 155閳?65 ppm. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Quality Control of 4-(Benzylamino)benzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts