Diels–Alder reactions of 4-phenyl-1,2,4-triazoline-3,5-dione

Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R.

doi:10.1039/j39670001905

Cited by 73 publications

(53 citation statements)

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“…It is known that the ratio of the type 21 and 22 adducts may depend on the dienophile activity and the reaction temperature .…”

Section: Resultsmentioning

confidence: 99%

“…This means that at the elevated temperature the rate of minor tautomer 20 formation (∂ C 20 /∂ t = k 7 → 20 · C 7 ) may be equal to or even greater than the observed consumption rate of dienophile 1 (–∂ C 1 /∂ t = k (7+1) , obs · C 7 · C 1 ). The adduct 22 was supposed in the reaction of 7+1 at 100°C , which means that the DA reaction of 1 goes with the tautomer bicyclo[4,2.0]oct‐2,4,7‐triene, 20 . This reaction has been reinvestigated in detail again at 100°C and at room temperature .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Cyclic and Acyclic N═N Bonds in Reactions with Some Alkenes and Dienes

Kiselev

Kornilov

Коновалов

2017

Int. J. Chem. Kinet.

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The kinetics of the Diels–Alder (DA) reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione 1, trans‐diethyl azodicarboxylate 2, and tetracyanoethene 3 with 1,3‐cyclohexadiene 4, cycloheptatriene 5, 1,3‐cycloheptadiene 6, cyclooctatetraene 7, and 1,3‐cyclooctadiene 8 in a range of temperatures and pressures has been studied. Values of the enthalpy, entropy, and volume of activation, as well as the enthalpy and volume of reaction have been obtained. Observed reaction rates of 5+1 and 7+1 have been compared with the known rate of norcaradiene 17 formation in the equilibrium 5⇌17, and that of bicyclo[4,2,0]‐octa‐2,4,7‐triene 20 in the equilibrium 7⇌20. The kinetic data show that the rate of formation of 17 from 5 is much greater than the loss rate of dienophile 1 in reaction of 5+1. In contrast, the formation rate of tautomer 20 is less than the loss rate of dienophile 1 in reaction of 7+1. This reflects that the consecutive reaction of 5 → 17 (+1) → 15 is possible whereas the consecutive reaction of 7 → 20 (+1) → 22 does not occur as the only way.

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“…It is known that the ratio of the type 21 and 22 adducts may depend on the dienophile activity and the reaction temperature .…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Cyclic and Acyclic N═N Bonds in Reactions with Some Alkenes and Dienes

Kiselev

Kornilov

Коновалов

2017

Int. J. Chem. Kinet.

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“…4-Substituted-1,2,4-triazoline-3,5-diones and bis(triazolinedione)s are among the most reactive dienophiles, [1][2][3][4][5][6][7][8][9][10][11][12] enophiles, 6 -12 and electrophiles. [13][14][15] Styrene undergoes facile reaction with triazolinediones as well as bis(triazolinedione)s and in the latter case leads to polymer formation via double Diels-Alder and Diels-Alderene sequences.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric polymerization via cycloaddition reactions

Mallakpour

Hajipour

Mahdavian

et al. 1999

J. Polym. Sci. A Polym. Chem.

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The reaction of N‐phthaloyl‐L‐leucine acid chloride (1) with isoeugenol (2) was carried out in chloroform, and novel optically active isoeugenol ester derivative 3 as a chiral monomer was obtained in high yield. Compound 3 was characterized by 1H‐NMR, IR, and mass and elemental analysis and then was used for the preparation of model compound 5 and polymerization reactions. 4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione, PhTD (4), was allowed to react with compound 3. The reaction is very fast and gives only one diastereomer of 5 via Diels–Alder and ene pathways in quantitative yield. In order to explain this diastereoselectivity, a nonconcerted two‐step mechanism involving benzylic cation (BC) and aziridinium (AI) have been proposed for the Diels–Alder and ene reactions, respectively. The polymerization reactions of novel monomer 3 with bis(triazolinedione)s [bis(p‐3,5‐dioxo‐1,2,4‐triazolin‐4‐ylphenyl)methane (8) and 1,6‐bis(3,5‐dioxo‐1,2,4‐triazolin‐4‐yl)hexane] (9)] were performed in N,N‐dimethylacetamide (DMAc) at room temperature. The reactions are exothermic, fast, and gave novel optically active polymers 10 and 11 via repetitive Diels–Alder–ene polyaddition reactions. These polymers have inherent viscosities in a range about 0.18–0.22 dL/g. Some physical properties and structural characterizations of these new polymers have been studied and are reported. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 1211–1219, 1999

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“…Although the vast majority of dienophiles, including the highly reactive tetracyanoethylene [7], and 4-phenyl-1,2,4-triazoline-3,5-dione [8], behaved similarly in their reactions with CHT, there are also some examples of CHT undergoing ene reactions in competition [9] or even in preference to the Diels-Alder reaction, such as in its reaction with diethyl azodicarboxylate (Scheme 4) [10].…”

Section: Introductionmentioning

confidence: 96%