The
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            lder Reaction with Maleic Anhydride*Present address, University of Southern California, Los Angeles, California.

Kloetzel, Milton C.

doi:10.1002/0471264180.or004.01

Cited by 14 publications

(14 citation statements)

References 265 publications

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“…Industrial product DCPD, reagent‐grade ethylene glycol, p ‐hydroxylphenyl methyl ether, and maleic anhydride were commercially available and used as received; nadic anhydride (NA) was prepared from maleic anhydride and cyclopentadiene, which was freshly cracked from its dimer DCPD just before its use according to the literature 23 . m ‐Chloroperoxybenzoic acid ( m ‐CPBA) was used as an epoxidizing agent, and methyl tetrahydrophthalic anhydride (MeTHPA) was used as a curing agent, no curing accelerator being added.…”

Section: Methodsmentioning

confidence: 99%

Long‐term remission after cessation of interferon‐α treatment in patients with severe uveitis due to Behçet's disease

Deuter¹,

Zierhut²,

Möhle³

et al. 2010

Arthritis & Rheumatism

166

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Objective. To retrospectively assess the development of visual acuity and the frequency and duration of relapse-free periods in patients who were treated with interferon-␣ (IFN␣) for severe uveitis due to Behçet's disease (BD) and who completed a followup period of >2 years.Methods. IFN alfa-2a was administered at an initial dosage of 6 million IU per day, then tapered to a maintenance dosage of 3 million IU twice per week, and finally discontinued, if possible. In case of a relapse, IFN treatment was repeated. Visual acuity at the end of followup was compared with visual acuity when ocular disease was in remission.Results. Of 53 patients (96 eyes), 52 (98.1%) responded to IFN. In 47 patients (88.7%), IFN could be discontinued when the disease was in remission. Twenty of these 47 (42.6%) needed a second treatment course during a median followup of 6.0 years (range 2.0-12.6 years). Visual acuity improved or remained unchanged in 91 eyes (94.8%). Ocular disease was still in remission in 50% of the patients 45.9 months after cessation of the first IFN course. The relapse rate tended to be lower in women than in men. The BD activity score decreased significantly during followup, but long-term remission of nonocular BD manifestations was not achieved. However, since local treatments were sufficient, no systemic treatment was administered.Conclusion. Our findings indicate that IFN␣ induces long-lasting remission in patients with severe ocular BD, resulting in a notable improvement in visual prognosis.

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Section: Methodsmentioning

confidence: 99%

Long‐term remission after cessation of interferon‐α treatment in patients with severe uveitis due to Behçet's disease

Deuter¹,

Zierhut²,

Möhle³

et al. 2010

Arthritis & Rheumatism

166

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“…These dienes include the following: ( E )‐1‐X‐butadienes (BDs) and 2‐X‐BDs, 1‐X‐cyclopentadienes (CPs) and 2‐X‐CP, α ‐X‐furans and β ‐X‐furans, α ‐X‐pyroles and β ‐X‐pyroles (their concerted exo and endo TSs are illustrated in chart ). It is known that numerous D–A reactions of different dienes with MA have been investigated experimentally and theoretically from different aspects,, but investigations of the substituent electronic effects on the endo–exo selectivity have been few documented in our knowledge.…”

Section: Introductionmentioning

confidence: 99%

Substituent effects in the Diels–Alder reactions of butadienes, cyclopentadienes, furans and pyroles with maleic anhydride

Qiu

2015

J of Physical Organic Chem

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In this study, activation energies in the Diels–Alder reactions of a series of substituted butadienes, cyclopentadienes, furans and pyroles with maleic anhydride were calculated by the M06‐2X/6‐31G(d) method. The substituent effects on the reactivity and the endo–exo selectivity have been examined. The strength of reactivity effect has an order of pyroles > furans > cyclopentadienes > butadienes, which is highly correlated with the lowest unoccupied molecular orbital energy, the electronic chemical potential and the electrophilicity of parent diene but relatively less correlated with the highest occupied molecular orbital energy and chemical hardness. The trend that an increase of necleophilicity caused by an electron‐donating group on the diene favors the endo TS is effective with C2 substitution. With C1 substitution, the trend is ambiguous or even opposite. Copyright © 2015 John Wiley & Sons, Ltd.

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“…Dipole moment of TS1a is 5.4 Debye which is higher than the dipole moments of the reacting species i.e., 4.4 Debye for maleic anhydride (2a) and 0.44 Debye for 7Hbenzo[a]phenalene (1a). TS1a leads to the formation of an unstable intermediate 3a [40] which has a dipole moment of 5.3 Debye. In the 2nd step, H28 is transferred from C12 to C17 resulting in formation of 2nd intermediate (4a).…”

Section: Resultsmentioning

confidence: 99%

“…The effect of electron donating and electron withdrawing substituents on activation barriers and energies of highest occupied orbitals and lowest occupied orbitals have been analyzed. Reactions of maleic anhydride with furans [37], anthracenes [38,39] and many other compounds have been very frequently studied experimentally and computationally but information available on reactions of 7H-benzo[a]phenalene (produced by the distillation of benzanthrone with zinc dust [40]) is very little. In fact, even a single report on computational study of its reaction could not be traced.…”

Section: Introductionmentioning

confidence: 99%

Quantum Mechanical Modeling Unveil the Effect of Substitutions on the Activation Barriers of the Diels-Alder Reactions of an Antiviral Compound 7H-Benzo[a]phenalene

Rehman

Mansha

Zahid

et al. 2021

Preprint

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Density functional theory has been utilized for exploring the mechanism of Diels-Alder reaction between 7H-benzo[a]phenalene and maleic anhydride. 7H-Benzo[a]phenalene is an antiviral compound and information available about its cycloaddition reactions with possible reaction path and mechanism is scarce. In order to work on the synthesis of its further potential derivatives, the mechanism of its reaction with all aspects should be well understood. Two novel intermediates involved in this reaction have been reported. Diels-Alder reaction of maleic anhydride has found many applications in the synthesis of wide range of useful products. The major concern of this work is to evaluate the consequences of introducing electron donating and electron withdrawing substituents on the reactivity of maleic anhydride towards 7H-benzo[a]phenalene. Thermodynamic parameters, activation parameters, energies of frontier orbitals, global reactivity indices and global electron density transfer (GEDT) have been determined for all the reactions. Fukui functions are computed for each reactant in order to identify the most reactive sites. All the reactions have been found to proceed via normal electron demand having polar nature. The substituents with opposite electronic properties were expected to affect the reactivity of dienophile in an inverse manner, however, the results are not according to this assumption. Rather, both kinds of substituents increased the activation barrier of the reaction. This behavior has been explained in the light of various parameters such as the stability of reacting species, gap of frontier molecular orbitals etc. Experimental studies reported previously are in agreement with these results.

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The D iels‐ A lder Reaction with Maleic Anhydride*Present address, University of Southern California, Los Angeles, California.

Cited by 14 publications

References 265 publications

Long‐term remission after cessation of interferon‐α treatment in patients with severe uveitis due to Behçet's disease

Long‐term remission after cessation of interferon‐α treatment in patients with severe uveitis due to Behçet's disease

Substituent effects in the Diels–Alder reactions of butadienes, cyclopentadienes, furans and pyroles with maleic anhydride

Quantum Mechanical Modeling Unveil the Effect of Substitutions on the Activation Barriers of the Diels-Alder Reactions of an Antiviral Compound 7H-Benzo[a]phenalene

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