Conversion of α‐Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid

@article{Hiegel2004ConversionO,
  title={Conversion of $\alpha$‐Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid},
  author={Gene A. Hiegel and Justin Cody Lewis and Jason W. Bae},
  journal={Synthetic Communications},
  year={2004},
  volume={34},
  pages={3449 - 3453}
}
Abstract Trichloroisocyanuric acid oxidation of α‐amino acids in water or methanol in the presence of pyridine produces nitriles with one less carbon in good yields and of high purity. 
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16 Citations

16 Citations

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References

SHOWING 1-7 OF 7 REFERENCES
Oxidation by persulphate. Part V. Silver-catalysed oxidation of secondary aliphatic amines and α-amino-acids
Silver-catalysed oxidation by cold aqueous persulphate, which converts primary aliphatic amines into aldehydes or ketones, gave poorer yields when applied to related secondary amines of the types…
SYNTHESIS OF OPTICALLY ACTIVE ALIPHATIC NITRILES FROM ALDEHYDES AND ACIDS
Abstract Optically active nitriles are very useful starting products for the preparation of chiral amines1, ketones2 and pyridines3. They are usually accessible from the corresponding acids via amide…
The Sadtler handbook of infrared spectra
Orthoesters and Related Compounds from Malono- and Succinonitriles
Products at the reaction of amino acids in aqueous solution with chlorine
24種類のアミノ酸と塩素との水溶液中における反応生成物を各フラクションに分けて, GCおよびGC/MSを用いて同定を行った。揮発性有機塩素化合物として, 多くのアミノ酸からクロロホルム, 四塩化炭素, トリクロロエチレン, クロロピクリンが検出された。ペンタン抽出物質として, 各アミノ酸の炭素数が1個少ないアルデヒドおよびニトリルが検出された。またフェニルアラニンの場合,…
Argentic oxide oxidations of organic compounds
One-step transformation of α-amino acids to α-amino aldehydes effected by electrochemical oxidation of Ph3P