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Transformation of aldehydes into nitriles in an aqueous medium using O-phenylhydroxylamine as the nitrogen source.

ABSTRACT: The conversion of an aldehyde into a nitrile can be efficiently performed using O-phenylhydroxylamine hydrochloride in buffered aqueous solutions. The reported method is specifically optimized for aqueous-soluble substrates including carbohydrates. Several reducing sugars including monosaccharides, disaccharides, and silyl-protected saccharides were transformed into cyanohydrins in high yields. The reaction conditions are also suitable for the formation of nitriles from various types of hydrophobic aldehyde substrates. Furthermore, cyanide can be eliminated from cyanohydrins, analogous to the Wohl degradation, by utilizing a readily-removed weakly basic resin as a promoter.

SUBMITTER: Cheewawisuttichai T

PROVIDER: S-EPMC8627682 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Transformation of aldehydes into nitriles in an aqueous medium using O-phenylhydroxylamine as the nitrogen source.

Cheewawisuttichai Thamrongsak T Hurst Robert D RD Brichacek Matthew M

Carbohydrate research 20210310

The conversion of an aldehyde into a nitrile can be efficiently performed using O-phenylhydroxylamine hydrochloride in buffered aqueous solutions. The reported method is specifically optimized for aqueous-soluble substrates including carbohydrates. Several reducing sugars including monosaccharides, disaccharides, and silyl-protected saccharides were transformed into cyanohydrins in high yields. The reaction conditions are also suitable for the formation of nitriles from various types of hydropho ...[more]

PMID: 33761407

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