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Reactions of the HCN‐Tetramer with Aldehydes
Author(s) -
Koch Klemens,
Schweizer W. Bernd,
Eschenmoser Albert
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790049
Subject(s) - chemistry , tetramer , aldehyde , aminal , acetaldehyde , aqueous solution , nitrile , organic chemistry , stereochemistry , catalysis , ethanol , enzyme
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.