Scholarship of Discovery
Benzofurazan 1 was reacted with 4,5-diphenyl-1,3-dioxol-2-one 2 in refluxing toluene. No reaction (NR) was detected by TLC analysis, as indicated below. It was decided that a higher-boiling solvent should be used. Accordingly, in the next trial, the same two reactants were used but this time with refluxing mesitylene as the solvent. A TLC analysis indicated a product was formed, but both reactants were still present in the reaction mixture. Another experiment with these conditions was run with a 30% excess of benzofurazan, to try to get all of the 4,5-diphenyl-1,3-dioxol-2-onetoreact. However, a TLC analysis of this reaction mixture showed the same results. A longer reflux of this run resulted in multiple products showing upon the TLC. In a final endeavor to push this reaction to completion (with reactants hopefully absent) but with a single product, refluxing 5-tert-butyl-m-xylene was used as the solvent, to see if the higher boiling point would make a difference. But, the TLC revealed two products in the reaction mixture along with some of the two reactants (still present). It was unclear as to if the expected product (3) was formed.
Armstrong, Douglas and Richey, Kristen, "Progress Toward the Synthesis of Novel Heterocyclic Compounds: Via Diels-Alder Reactions, Including Microwave Promotion" (2015). Faculty Scholarship – Chemistry. 7.
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