Reactions of the HCN-tetramer with aldehydes |
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| Authors: | Koch Klemens Schweizer W Bernd Eschenmoser Albert |
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| Institution: | 1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), H?nggerberg HCI, Wolfgang‐Pauli‐Strasse 10, CH‐8093 Zürich;2. Dorfstrasse 13, CH‐2572 Sutz. The work described here is one of the four parts of the thesis: Klemens Koch, Promotionsarbeit ETH‐Zürich, 1989–1992 [2] (Chapt. 3: ‘Die aldehydkatalysierte Hydratisierung von Blaus?ure‐Oligomeren’, p.?33–61);3. the full text of the thesis can be downloaded from the internet: http://e‐collection.ethbib.ethz.ch/show?type=diss&nr=9968. |
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| Abstract: | The HCN-tetramer, a 'classic' of the prebiotic chemistry of HCN, is shown to undergo a remarkable reaction with acetaldehyde in slightly basic or neutral aqueous solution at room temperature. The reaction consists in an aldolization-type C,C-bond formation, accompanied by a (presumably aldehyde-catalyzed) hydration of one of the two nitrile groups and the formation of two cyclic aminal-type groupings, each of the latter incorporating an additional molecule of the aldehyde. Should this so far unexplored type of chemistry of the HCN-tetramer prove to have some generality, the finding might add a new dimension to the potential etiological relevance of this HCN-oligomer. |
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| Keywords: | HCN‐Tetramer Prebiotic chemistry Catalysis intramolecular Aminal formation Nitrile hydrolysis |
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