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Research Article Open access CC BY 4.0

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

Gary W. Breton

Organics · pp. 164–172 · Published 17 Apr 2023

10.3390/org4020013

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., <−60 °C). This reactivity has been exploited recently for novel synthetic applications. It was previously reported that no reaction between MeTAD and benzene occurs at room temperature. However, it has now been discovered that MeTAD reacts effectively with benzene upon visible light irradiation over a several day period at room temperature. The major product is a 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.

Benzene Photochemistry Chemistry Adduct Cycloaddition Reactivity (psychology) Benzene derivatives Electrophile

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Cited by 2

Recent Developments in the Photochemical Reactions of N‐Heterocyclic Compounds

Jayaveerapandiyan Barathkumar, Rohan Gupta, Subbiah Nagarajan · European Journal of Organic Chemistry · 2024

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