4-Phenyl-1,2,4-triazolin-3,5-dione: a powerful dienophile

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

doi:10.1016/s0040-4039(00)70917-8

Cited by 130 publications

(63 citation statements)

References 13 publications

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“…A comparison of the k2 values (towards cyclopentadiene at 20 "C in dioxane) in the series (68)-(71) shows that the double bond indicated is more strongly activated by the cyclic structural elements in the compounds (68) to (70) than by a cis-dinitrile arrangement in the dinitrile of maleic acid (71). The replacement of one cis-dinitrile grouping in TCNE by the stronger activating groups in (68)- (70) should lead to very active dienophiles.…”

Section: --mentioning

confidence: 99%

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Diels‐Alder reactions II: The Reaction Mechanism

Sauer¹

1967

Angew. Chem. Int. Ed. Engl.

512

130

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Section: --mentioning

confidence: 99%

“…The replacement of one cis-dinitrile grouping in TCNE by the stronger activating groups in (68)- (70) should lead to very active dienophiles. This expectation is fulfilled by p-benzoquinone-2,3-dicarboxylic anhydride and by dicyanomaleimide, which sometimes add much more rapidly than TCNE to the dienes of Table 7 [671.…”

Section: --mentioning

confidence: 99%

Diels‐Alder reactions II: The Reaction Mechanism

Sauer¹

1967

Angew. Chem. Int. Ed. Engl.

512

130

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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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“…However, with PTAD, one of the most reactive dienophiles known, 16 it became possible to realize a Diels-Alder cycloaddition of [4]ferrocenophane 4, for which one might, however, consider not only a synchronous, but a stepwise process as well. Cycloadduct 12 was obtained in 68% yield as a bright yellow solid (Scheme 6).…”

Section: Figurementioning

confidence: 99%

New Phenoxy[4]ferrocenophanedienes: First Case of a Boat Conformation of a Diazacyclohexene 1,4-Capped by a Ferrocene

Krauße

Butenschön

2015

Synlett

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Some new aryloxy [4]ferrocenophanedienes are described, which have been obtained by reaction of 1,1′-di(1-propynyl)ferrocene and respective phenols. These include one case of a twofold reaction of this type. The possibility of using the products as substrates in Diels-Alder cycloadditions was evaluated with the result that only the most reactive dienophile, 4-phenyl-1,2,4-triazoline-3,5-dione, underwent this reaction. The cycloadduct has an unprecedented structure in that the ferrocene moiety 1,4-diaxially caps a boat conformer of a cyclohexane moiety.

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4-Phenyl-1,2,4-triazolin-3,5-dione: a powerful dienophile

Cited by 130 publications

References 13 publications

Diels‐Alder reactions II: The Reaction Mechanism

Diels‐Alder reactions II: The Reaction Mechanism

Asymmetric polymerization via cycloaddition reactions

New Phenoxy[4]ferrocenophanedienes: First Case of a Boat Conformation of a Diazacyclohexene 1,4-Capped by a Ferrocene

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