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Updated: Jul 1, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Isocyanurate anion radicals via electron-initiated cycloaddition of isocyanates
Steven J Peters1, Joseph R Klen, Nathaniel C Smart
1Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA. sjpeter@ilstu.edu
Abstract:
Room temperature sodium metal reductions of alkyl isocyanates lead to the rapid electron-initiated formation of alkyl isocyanurate anion radicals, which exhibit EPR coupling to only two equivalent nitrogens. Reduction of (13)C-enriched ethyl isocyanate reveals that the odd electron localizes in the pi system of one carbonyl in the isocyanurate ring. EPR line-width alternation effects indicate that at least two stable conformers are in rapid equilibrium undergoing fast exchange.
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