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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Glycolonitrile oligomerization: structure of isolated oxazolines, potential heterocycles on the early earth
G Arrhenius1, K K Baldridge, S Richards-Gross
1Department of Chemistry, University of California, San Diego, La Jolla 92093-0358, USA.
Abstract:
A study of glycolonitrile polymerization has led to the isolation and characterization of two 2,5-dihydro-4-aminooxazoles, 4 and 5. Previous reports have misassigned these structures as s-triazines or pyrimidines. X-ray diffraction analysis of crystals of 4 and an acetylated oxazole derivative of 5 (6) confirm the proposed structures. Ab initio computations are used to assess the relative thermodynamic stability of three trimer isomers (an s-triazine, an aminohydroxypyrimidine, and an aminooxazoline), and the results indicate that 4 is a novel kinetic product. Mechanistic considerations rationalize kinetic oxazole formation over the more customary triazine or pyrimidine trimers.
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