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RESEARCH PRODUCT
Programmed Formation of HCN Oligomers through Organosulfur Catalysis
Caroline GrundkeTill OpatzD. Tyler McquadeChristopher J. KampfCaleb J. KongB. Frank Guptonsubject
Spectrometry Mass Electrospray IonizationChemistry PharmaceuticalElectrospray ionizationOrganic ChemistryCationic polymerizationCombinatorial chemistryCatalysisCatalysischemistry.chemical_compoundchemistryTetramerDiaminomaleonitrileMoleculeDisulfidesOrganosulfur compoundsAcetone cyanohydrindescription
An efficient, inexpensive, and reliable synthesis of diaminomaleonitrile (DAMN, 1) is described starting from readily available acetone cyanohydrin as the source of hydrogen cyanide (HCN). Diaminomaleonitrile (DAMN) is known to be an important intermediate in heterocyclic and medicinal chemistry as well as being a possible precursor for the origin of life's hypothesis within prebiotic chemistry. The mechanism of its formation through organosulfur catalysis has been investigated by electrospray ionization mass spectrometry (ESI-MS) using two newly synthesized cationic "marker" molecules as a tool that allows for sensitive detection. As a result, the proposed mechanism of a thiocyanate-mediated synthesis of the HCN tetramer DAMN starting from organic disulfides was confirmed.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-07-12 | The Journal of Organic Chemistry |