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. 2021 Aug 6;86(15):10320-10329.
doi: 10.1021/acs.joc.1c01023. Epub 2021 Jul 12.

Programmed Formation of HCN Oligomers through Organosulfur Catalysis

Caroline Grundke  1 , Caleb Kong  2 , Christopher J Kampf  1 , B Frank Gupton  2 , D Tyler McQuade  2 , Till Opatz  1
Affiliations

Programmed Formation of HCN Oligomers through Organosulfur Catalysis

Caroline Grundke et al. J Org Chem. .

Abstract

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.

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