70332-87-5

Upstream product

• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 4453-90-1 1,4-dihydro-1,4-methanonaphthalene 
• 10316-56-0 9,10-(4’-phenyl)urazolo-9,10-dihydroanthracene 
• 678197-26-7 tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-diol 
• 112655-15-9 3β,7β-bis(methoxycarbonyloxy)-endo-tricyclo<6.2.1.0^2.7>undeca-4,9-diene 
• 90461-90-8 C₂₈H₃₃N₃O₂ 

Relevant academic research and scientific papers

A novel palladium-catalyzed deoxygenation of enediols to 1,3-dienes

Hydroxylative Knoevenagel condensation of aldehydes followed by reduction provides a simple entry to 1,4-enediols. Subjecting the dicarbonate to a palladium(0) catalyst in the presence of triisopropyl phosphite achieves a mild vinylogous deoxygenation to (E)-1,3-dienes. Stereocontrolled synthesis of the sex pheromone of the red bollworm moth, (E)-9,11-dodecadienyl acetate, and a formal synthesis of the cotton boll weevil antifeedant, α-eleostearic acid, demonstrate the utility of this new methodology.

Synthesis of Urazoles via Cycloaddition Employing 4-Phenyl-4H-1,2,4-Triazole-3,5-dione (PTAD) Transfer

A new method was developed involving transfer of 4-phenyl-4H-1,2,4-triazole-3,5-dione (PTAD) from thermally labile urazoles 9 and 10 to bicyclic olefin derivatives 1-8, which irreversibly undergo cycloaddition accompanied by Wagner-Meerwein rearrangement.In most cases purer products and significantly improved yields of the corresponding urazoles 11-18 are obtained than by direct PTAD cycloaddition.

On the Mechanism of the Formation of Rearrangement Products in the Addition of Arenesulfenyl Chloride and 4-Phenyl-4H-1,2,4-triazole-3,5-dione to Benzonorbornadienes

On the basis of product and rate studies the similarity in the electrophilic addition of phenyltriazolediones (PTAD) and the arenesulfenyl chlorides 10 and 11 to benzonorbornadienes 1, 8, and 9, giving the rearrangement products 2 and 6, respectively, is being recognized.In analogy to the established mechanism involving three-center electrophilic attack for the arenesulfenyl chloride reaction, the PTAD reaction is proposed to proceed via the aziridinium ion 4 as intermediate.The lack of trapping, of regioselectivity and of formation of addition product in the case ofPTAD is interpreted in terms of electronic and steric effects on the dipolar aziridinium species. - An X-ray analysis of the addition product 17, derived from 9 and 11, is reported.