Reinvestigation of the Room Temperature Photochemical Reaction between <i>N</i>-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) and Benzene

Abstract

The photochemical reaction of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with benzene is known to lead to a Diels–Alder cycloaddition product when conducted at low temperatures (i.e., para-substituted bisurazole adduct. Our studies indicate that the adduct is formed via sequential aromatic substitution reactions made possible by electron transfer from the aromatic ring to the highly electrophilic triplet state of photoactivated MeTAD.

Keywords

• <i>N</i>-methyl-1,2,4-triazoline-3,5-dione
• MeTAD
• Diels–Alder
• benzene
• photochemistry