Reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with conjugated dienes

Gillis, Bernard T.; Hagarty, Jack D.

doi:10.1021/jo01288a016

Cited by 76 publications

(26 citation statements)

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“…Adduct 25 b (115 mg, 80 %) was obtained as a pale yellow solid. All spectral data of 25 b were in complete agreement with those of a sample independently prepared from diene 8 b and 24 b according to the literature 45…”

Section: Methodssupporting

confidence: 75%

“…Addition of diethyl ether and centrifugation of the thus‐formed suspension of 7 afforded the Pd II complex in 82 % yield. The solution of the diene 8 b in CH 2 Cl 2 /Et 2 O also containing dba was treated with dienophiles 24 a and 24 b following the careful removal of diethyl ether at normal pressure, which furnished cycloadducts 25 a 44 and 25 b 45 in 75 and 80 % yield, respectively. Reaction of 8 b with the dienophiles in the presence of diethyl ether was very slow.…”

Section: Resultsmentioning

confidence: 99%

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Selective Rearrangements of Quadruply Hydrogen‐Bonded Dimer Driven by Donor–Acceptor Interaction

Wang

Shao

et al. 2003

Chemistry A European J

106

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A general method has been developed to control the selective rearrangement of Meijer's AADD quadruply hydrogen-bonded homodimers by introducing an additional donor-acceptor interaction. Therefore, one donor-assembling monomer, 1, in which the electron-rich bis(p-phenylene)-34-crown-10 moiety is connected to the hydrogen-bonding moiety, and two acceptor-assembling monomers, 2 and 3, in which the electron-deficient pyromellitic diimide or naphthalene diimide group is incorporated, respectively, are synthesized and characterized. 1H NMR and 2D-NOESY studies show that all these compounds exist as stable homodimers in chloroform. Mixing 1 equiv of 1 with 1 equiv of 2 in chloroform leads to the formation of heterodimers 1.2 in approximately 60 % yield, as a result of the electrostatic interaction between the bis(p-phenylene)-34-crown-10 moiety of 1 and the pyromellitic diimide group of 2. Selective formation of heterodimer 1.3 (>97 %) was achieved by mixing 1 equiv of 1 with 1 equiv of 3 in chloroform which resulted in a strengthened electrostatic interaction between the bis(p-phenylene)-[34]crown-10 moiety of 1 and the naphthalene diimide group of 3. The structures of heterodimers 1.2 and 1.3, which have been characterized by 1H NMR and UV/Vis experiments, reveal a remarkable promoting effect between the donor-acceptor interaction and intermolecular hydrogen-bonding. 1H NMR studies also reveal that heterodimers 1.2 and 1.3 can be fully and partially dissociated by addition of heterocycle 29, leading to the formation of new more robust heterodimers 1.29 and 2.29, or 3.29,respectively, and partially regenerated by subsequent addition of heterocyclic compound 30 through the formation of a new heterodimer 29.30. Heterodimers 1.2 and 1.3 represent a novel class of pseudo[2]rotaxanes constructed by two different noncovalent interactions.

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Section: Methodssupporting

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Selective Rearrangements of Quadruply Hydrogen‐Bonded Dimer Driven by Donor–Acceptor Interaction

Wang

Shao

et al. 2003

Chemistry A European J

106

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“…The title compound has not been described before, It was synthesized (Hameeteman, de Man & Altona, 1972) from a known precursor, the 8,9-unsaturated compound (Gillis & Hagarty, 1967), via a hydrogenation procedure as decribed by Askani (1965). The compound was recrystallized from methanol in the form of transparent irregular blocks.…”

Section: Methodsmentioning

confidence: 99%

Conformation of non-aromatic ring compounds. LXXXVI. The crystal and molecular structure of 4-phenyl-2,4,6-triazatricyclo[5,2,2,0^2,6]undecane-3,5-dione at –170°C

Ende¹,

Offereins²,

Romers³

1974

Acta Crystallogr Sect B

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“…In the case of reactions of active dienes with diethyl azodicarboxylate ( 1 ) or 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione ( 2 ), the major products are the [4+2]‐cycloadducts with their stereospecificity preserved. In the case of less active dienes such as 1,3‐cyclohexadiene and Z , Z ‐1,4‐disubstituted‐1,3‐butadienes , the ene reactions of 1 successfully compete with the DAR.…”

Section: Introductionmentioning

confidence: 99%

Reactivity of 4-Phenyl-1,2,4-triazoline-3,5-dione and Diethylazocarboxylate in [4+2]-Cycloaddition and Ene Reactions: Solvent, Temperature, and High-Pressure Influence on the Reaction Rate

Kiselev

Kornilov

Lekomtseva

et al. 2015

Int. J. Chem. Kinet.

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We have studied the solvent, temperature, and pressure influences on the reaction rates of cyclic and acyclic N=N bonds in the Diels-Alder and ene reactions. The transfer from N-phenylmaleimide (9) to a structural analogue, 4-phenyl-1,2,4-triazoline-3,5-dione (2), is accompanied by the rate increase in five to six orders of magnitude in the Diels-Alder reactions with cyclopentadiene (4) and 9,10-dimethylanthracene (5), whereas the transfer from dimethyl fumarate (10) to diethyl azodicarboxylate (1) increases only in one to two orders of magnitude. The ratio of the reaction rate constants (2 + 4)/(1 + 4) is very large (5.2 × 10 7 ) and almost the same (5.3 × 10 7 ) as in the ene reactions with tetramethylethylene (7),

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Reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with conjugated dienes

Cited by 76 publications

References 0 publications

Selective Rearrangements of Quadruply Hydrogen‐Bonded Dimer Driven by Donor–Acceptor Interaction

Selective Rearrangements of Quadruply Hydrogen‐Bonded Dimer Driven by Donor–Acceptor Interaction

Conformation of non-aromatic ring compounds. LXXXVI. The crystal and molecular structure of 4-phenyl-2,4,6-triazatricyclo[5,2,2,0^2,6]undecane-3,5-dione at –170°C

Reactivity of 4-Phenyl-1,2,4-triazoline-3,5-dione and Diethylazocarboxylate in [4+2]-Cycloaddition and Ene Reactions: Solvent, Temperature, and High-Pressure Influence on the Reaction Rate

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Reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with conjugated dienes

Cited by 76 publications

References 0 publications

Selective Rearrangements of Quadruply Hydrogen‐Bonded Dimer Driven by Donor–Acceptor Interaction

Selective Rearrangements of Quadruply Hydrogen‐Bonded Dimer Driven by Donor–Acceptor Interaction

Conformation of non-aromatic ring compounds. LXXXVI. The crystal and molecular structure of 4-phenyl-2,4,6-triazatricyclo[5,2,2,02,6]undecane-3,5-dione at –170°C

Reactivity of 4-Phenyl-1,2,4-triazoline-3,5-dione and Diethylazocarboxylate in [4+2]-Cycloaddition and Ene Reactions: Solvent, Temperature, and High-Pressure Influence on the Reaction Rate

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Conformation of non-aromatic ring compounds. LXXXVI. The crystal and molecular structure of 4-phenyl-2,4,6-triazatricyclo[5,2,2,0^2,6]undecane-3,5-dione at –170°C