Programmed Formation of HCN Oligomers through Organosulfur Catalysis.
| Autor: | Grundke C; Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany., Kong C; Department of Chemical and Life Science Engineering, Virginia Commonwealth University, Richmond, Virginia 23220, United States., Kampf CJ; Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany., Gupton BF; Department of Chemical and Life Science Engineering, Virginia Commonwealth University, Richmond, Virginia 23220, United States., McQuade DT; Department of Chemical and Life Science Engineering, Virginia Commonwealth University, Richmond, Virginia 23220, United States., Opatz T; Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany. |
|---|---|
| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2021 Aug 06; Vol. 86 (15), pp. 10320-10329. Date of Electronic Publication: 2021 Jul 12. |
| DOI: | 10.1021/acs.joc.1c01023 |
| Abstrakt: | 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. |
| Databáze: | MEDLINE |
| Externí odkaz: |
|