Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 

Saved Queries

Sign in to use this feature.

Search Filter Reset All

Years

Between: -

Subjects

remove_circle_outline
Add Subjects Reset
Select Subjects

Journals

remove_circle_outline
Add Journals Reset
Select Journals

Article Types

remove_circle_outline
Add Article Types Reset
Select Article Types

Countries / Regions

remove_circle_outline
Add Countries / Regions Reset
Select Countries / Regions
Update Search
share announcement

Search Results (2)

Search Parameters:
Keywords = N-methyl-1,2,4-triazoline-3,5-dione

Order results
Result details
Results per page
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
9 pages, 1162 KiB  
Article
Reinvestigation of the Room Temperature Photochemical Reaction between N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) and Benzene
by Gary W. Breton
Organics 2023, 4(2), 164-172; https://doi.org/10.3390/org4020013 - 17 Apr 2023
Cited by 1 | Viewed by 2109
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Chemistry of Heterocycles)
►▼ Show Figures

Figure 1

8 pages, 1322 KiB  
Article
Exploring the Limits of Reactivity of N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) with Disubstituted Bicycloalkadienes in the Homo-Diels–Alder Reaction
by Gary W. Breton and Kenneth L. Martin
Organics 2023, 4(1), 41-48; https://doi.org/10.3390/org4010002 - 31 Dec 2022
Cited by 1 | Viewed by 2686
Abstract
The [2+2+2] cycloaddition (homo-Diels–Alder reaction) of N-substituted 1,2,4-triazoline-3,5-diones (TADs) with bicycloalkadienes produces strained heterocyclic compounds. A reaction with the unsubstituted dienes occurs readily to produce only the expected homo-Diels–Alder adducts. However, previous work in the literature showed that the attachment of a [...] Read more.
The [2+2+2] cycloaddition (homo-Diels–Alder reaction) of N-substituted 1,2,4-triazoline-3,5-diones (TADs) with bicycloalkadienes produces strained heterocyclic compounds. A reaction with the unsubstituted dienes occurs readily to produce only the expected homo-Diels–Alder adducts. However, previous work in the literature showed that the attachment of a single electron-withdrawing group to the diene system results in the formation of not only the expected homo-Diels–Alder adducts, but also interesting “insertion” products. To probe the limits of reactivity of these diene systems, we investigated the reaction of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with bicycloalkadienes substituted with two electron-withdrawing groups, i.e., two carbomethoxy or two cyano groups. We hoped to learn whether the reaction still proceeded, and if so, whether the homo-Diels–Alder adducts and/or other types of products were formed. We found that a reaction between MeTAD and the dienes takes place upon substitution with two carbomethoxy groups, albeit at a considerably slower rate than other reactions. The only products observed were the homo-Diels–Alder adducts. However, attachment of two CN groups completely inhibited reactivity. Full article
(This article belongs to the Collection Advanced Research Papers in Organics)
►▼ Show Figures

Figure 1

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying article 1-50 on page 1 of 1.
Back to TopTop