Issue 39, 2017

The trimerization of acetylenes involves a cascade of biradical and pericyclic processes

Abstract

Thorough computational studies were performed on mechanisms and energies for the thermal trimerizations of neutral or electron-rich acetylenes used as cross-linkers in organic hard-masks for lithography applications. These studies indicate that the operative mechanism proceeds through initial cyclobutadiene formation via a biradical mechanism. Cyclobutadienes form Dewar benzenes via Diels–Alder cycloadditions, or biradical processes, or both, before producing benzenes by electrocyclic ring-opening reactions. These pathways are preferred to alternatives involving concerted trimerizations or mechanisms involving carbene intermediates.

Graphical abstract: The trimerization of acetylenes involves a cascade of biradical and pericyclic processes

Supplementary files

Article information

Article type
Paper
Submitted
29 ก.ค. 2560
Accepted
18 ก.ย. 2560
First published
18 ก.ย. 2560

Org. Biomol. Chem., 2017,15, 8326-8333

The trimerization of acetylenes involves a cascade of biradical and pericyclic processes

G. O. Jones and Z. J. Krebs, Org. Biomol. Chem., 2017, 15, 8326 DOI: 10.1039/C7OB01885A

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