130780-93-7Relevant academic research and scientific papers
Chemistry of alpha-aminonitriles. Aziridine-2-carbonitrile: photochemical formation from 2-aminopropenenitrile
Drenkard,Ferris,Eschenmoser
, p. 1373 - 1390 (2007/10/02)
2-Aminopropenenitrile in solvents such as MeCN, MeOH, or H2O is photoisomerized by UV light to racemic aziridine-2-carbonitrile (rac-2); the larger part of the starting material, however, fragments to HCN and MeCN. The observed photocyclization constitutes a structural connection within an ensemble of C3H4N2 compounds considered to be potentially relevant to prebiotic chemistry.
Chemistry of α-Aminonitriles. Aziridin-2-carbonitrile, a Source of Racemic O3-Phosphonoserinenitrile and Glycolaldehyde Phosphate
Wagner, Ernst,Xiang, Yi-Bin,Baumann, Karl,Gueck, Juergen,Eschennmoser, Albert
, p. 1391 - 1409 (2007/10/02)
Racemic aziridine-2-carbonitrile (rac-1) in MeCN solution reacts regioselectively (>90percent) with 2 equiv. of TsOH at room temperature to form the hydrotosylate of racemic O3-tosylserinenitrile (rac-2) via a β-ring opening (Scheme 2).A similar regioselective reaction takes place between rac-1 and H3PO4 to produce racemic O3-phosphoserinenitrile (rac-3) which is in turn a source of glycolaldehyde phosphate (=formylmethyl dihydrogenphosphate) under the conditions of a 'retro-Strecker' reaction in aqueous solution (Scheme 6).These experiments document a close structural relationship between the simplest of the sugar phosphates and an α-aminonitrile precursor.
