Ene reaction of triazolinediones with alkenes. 1. Structure and properties of products

Ohashi, Shigeru; Leong, K. N.; Matyjaszewski, Kristoff; Butler, George B.

doi:10.1021/jo01305a020

Cited by 78 publications

(48 citation statements)

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“…[10] However, an ESR signal could not be detected at room temperature in solutions, not only in diethyl ether but also in a wide variety of solvents (dichloromethane, acetonitrile, tetrahydrofuran, diisopropyl ether), as reported for PTAD by different authors. [1,10,27] It was therefore concluded that the methyl urazolyl radical is much too reactive in solution at room temperature to be studied directly by ESR. The single radical species that is stable enough to be investigated by ESR spectroscopy in solution, at room temperature, is the anion-radical, which is proposed as the intermediate in the thermal reaction of MTAD leading to the deazadimer by Borhani and Greene.…”

Section: Esr Experimentsmentioning

confidence: 99%

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Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

et al. 2000

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The photoaddition of 4‐methyl‐1,2,4‐triazoline‐3,5‐dione (4‐MTAD) with a wide variety of acyclic, cyclic and crown aliphatic ethers has been investigated. Monochromatic (λ = 514.5 nm) or polychromatic (λ ≥ 310 nm) irradiations give identical mono‐urazolyl ethers as reaction products. Unsymmetrical acyclic ethers afford a mixture of the two α and α′ mono‐urazolyl ethers. In the case of 12‐crown‐4, mono and di‐substituted products are obtained. ESR experiments and quantum calculations at the AM1 and 6‐31G* levels were performed and a possible reaction mechanism is proposed in which the most probable photochemical process is the H‐abstraction leading to a urazolyl radical.

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Section: Esr Experimentsmentioning

confidence: 99%

“…4-Substituted-1,2,4-triazoline-3,5-diones (4-RTAD) are cyclic electron deficient azo compounds that readily react thermally with olefinic [1][2][3][4][5][6] and dienic [7][8][9] sites. As such they have been employed as intermediates in the synthesis of a wide variety of heterocyclic systems.…”

Section: Introductionmentioning

confidence: 99%

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

et al. 2000

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“…1 (TMS) was used as an internal reference. Proton resonances were designated as singlet (s), doublet (d), doublet of doublet (dd), and multiplet (m).…”

Section: Materials and Equipmentmentioning

confidence: 99%

Synthesis and characterization of new polyamides derived from 4‐(4′‐aminophenyl)urazole and aliphatic diacid chlorides

Mallakpour

Rafiee

2004

J of Applied Polymer Sci

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4-(4Ј-Aminophenyl)urazole (AmPU) was prepared from 4-nitrobenzoic acid in six steps. The reaction of AmPU with acetyl chloride was performed in N,N-dimethylacetamide solutions at different ratios, and the resulting disubstituted and trisubstituted amide derivatives were obtained in high yields and were used as models for polymerization reactions. Polycondensation reactions of AmPU with succinyl chloride, suberoyl chloride, and sebacoyl chloride were performed with conventional solution polymerization techniques in the presence of different catalysts, such as pyridine, triethylamine, and dibutyltin dilaurate, and led to the formation of novel aliphatic polyamides. The resulting novel polyamides had inherent viscosities of 0.11-0.22 dL/g in dimethylformamide or H 2 SO 4 at 25°C. These polyamides were characterized with IR, 1 H-NMR, elemental analysis, and thermogravimetric analysis. Some physical properties and structural characterization of these novel polyamides are reported.

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“…It has a value of 4É71, which is almost the same as that of pK a acetic acid. 3 The urazolyl group from compound (3) also has two NwH protons which are acidic.…”

Section: Introductionmentioning

confidence: 99%

“…The purpose of this investigation was to synthesize compound (3) and to use it as a monomer for the synthesis of novel polymers.…”

Section: Introductionmentioning

confidence: 99%

Polymerization of 1-methyl-2,5-bis[1-(4-phenylurazolyl)] pyrrole dianion with alkyldihalides

1998

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1‐Methyl‐2,5‐bis[1‐(4‐phenylurazolyl)] pyrrole was prepared from the reaction of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione with N‐methylpyrrole in methylene chloride solution. This compound was converted to its potassium dianion salt upon reaction with potassium hydroxide in absolute ethanol. The reaction of this dianion salt with excess methyl iodide in dimethyl sulphoxide gave the methylated adduct in high yield. Polymerizations of this dianion salt with 1,2‐dibromoethane, 1,2‐diiodoethane and 1,4‐diiodobuthane were performed in dimethyl sulphoxide and led to the formation of new polymers. Some structural characterization and physical properties of these novel polymers are reported. © 1998 SCI.

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Ene reaction of triazolinediones with alkenes. 1. Structure and properties of products

Cited by 78 publications

References 0 publications

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

Synthesis and characterization of new polyamides derived from 4‐(4′‐aminophenyl)urazole and aliphatic diacid chlorides

Polymerization of 1-methyl-2,5-bis[1-(4-phenylurazolyl)] pyrrole dianion with alkyldihalides

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