Dien‐Synthesen des 2.3‐Dihydro‐naphthalins und des Naphthalins mit <i>N</i>‐Phenyl‐maleinimid

Dinulescu, I. G.; Avram, Margarete; Nenitzescu, Costin D.

doi:10.1002/cber.19600930816

Cited by 16 publications

(4 citation statements)

References 9 publications

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“…For example, naphthalene reacts with the N-phenyl-maleimide only under high-pressure conditions. Despite high pressure as well as higher temperature, the conversion of addends is realized in 80 h (Scheme 3) [9].…”

Section: Introductionmentioning

confidence: 99%

“…The aim of this work is to enhance the understand and the description of bonding breaking/forming involved on the mechanism of the DA reactions, in particular in cycloadditions involving very stable reagents as aromatic species; hence, we present a complete study of the DA reaction given by a strong electrophile as perfluorobicyclo[2.2.0] Scheme 1 DA reaction of furan with (E)-3,3,3-trichloro-1-nitroprop-1-ene [2] Scheme 2 DA reaction between anthracene and (E)-3,3,3trichloro-1-nitroprop-1-ene [8] Scheme 3 DA reaction naphthalene with N-phenylmaleimide [9] Scheme 4 DA reaction of perfluorobicyclo[2.2.0]hex-1(4)-ene with benzene [12] hex-1(4)-ene 1a with benzene 2a and naphthalene 2b and, on the other hand, the corresponding DA reaction mechanism given by the marginal electrophile as bicyclo[2.2.0] hex-1(4)-ene 1b with benzene 2a and naphthalene 2b. To achieve that will be used known theoretical tools defined within the context of the density functional theory (DFT) [20,21].…”

Section: Introductionmentioning

confidence: 99%

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Perfluorobicyclo[2.2.0]hex-1(4)-ene as unique partner for Diels–Alder reactions with benzene: a density functional theory study

Kącka‐Zych

Pérez

2021

Theor Chem Acc

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The mechanism of the Diels–Alder reactions between perfluorobicyclo[2.2.0]hex-1(4)-ene (1a) and bicyclo[2.2.0]hex-1(4)-ene (1b) with benzene (2a) and naphthalene (2b) has been studied within the density functional theory at the MPWB1K/6-311G(d,p) level. The bonding pattern in these reactions is analyzed in the topology of the electron localization function within the bonding evolution theory perspective. The bonding electron density changes along the reaction paths reveal that the C–C bond formation takes place through a synchronous and non-concerted one-step mechanism and proceeds with a moderate activation energy. The reactivity order with 1a is 2a–2b. The reactions begin by the rupture of the double bond in the strained 1a-b molecules, and then two pseudoradical centers at the 1a-b fragments are created. Finally, at the same time, two new single bonds are formed in the cycloaddition products. The TSs proceed with high global electron density transfer providing a polar character at these reactions.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Perfluorobicyclo[2.2.0]hex-1(4)-ene as unique partner for Diels–Alder reactions with benzene: a density functional theory study

Kącka‐Zych

Pérez

2021

Theor Chem Acc

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“…Thus, 1,4-dibromo-1,2,3,4-tetrahydronaphthalene was synthesized by refluxing 1,2,3,4-tetrahydronaphthalene with N-bromosuccinimide in carbon tetrachloride in the presence of benzoyl peroxide (Scheme 2). [19] This bromination reaction was completed before any appreciable dehydrobromination to naphthalene took place. The dibromotetralin derivative was immediately reacted with freshly prepared borane-protected lithium diphenylphosphide to give the borane-protected diphosphine, which upon treatment with pyrrolidine yielded the desired ligand 4.…”

Section: Resultsmentioning

confidence: 99%

“…Next, we attempted the synthesis of ligands with a tetralin backbone. Thus, 1,4‐dibromo‐1,2,3,4‐tetrahydronaphthalene was synthesized by refluxing 1,2,3,4‐tetrahydronaphthalene with N ‐bromosuccinimide in carbon tetrachloride in the presence of benzoyl peroxide (Scheme ) 19. This bromination reaction was completed before any appreciable dehydrobromination to naphthalene took place.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of New Diphosphine Ligands and their Application in Pd‐Catalyzed Alkoxycarbonylation Reactions

Pews‐Davtyan¹,

Fang²,

Jackstell³

et al. 2014

Chemistry An Asian Journal

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Carbocyclic and N-heterocyclic analogues of the industrially applied ligand bis(di-tert-butylphosphinomethyl)benzene (1) have been synthesized in moderate to very good yields. The new ligands are based on benzene, tetralin, lutidine, pyrazine, quinoxaline, and maleimide backbones. Electronic and steric variations of the phosphorous donor sites were performed. As a benchmark reaction, the palladium-catalyzed methoxycarbonylation of 1-octene has been tested. Ester yields up to 64% and high linear selectivities up to 92% were achieved.

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Diels‐Alder‐Reaktionen I: Präparative Aspekte

Sauer

1966

Angewandte Chemie

128

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Seit fast 40 Jahren beanspruchen die nach ihren Entdeckern benanntenCycloadditio;?en konjugierter Diene praparatives und mechanistisches Interesse. Die fast unerschopjliche Variierbarkeit der Komponenten dieser Einstufenreaktionen bietet Zugang zu wichtigen Verbindungsklassen. Die in dcesem Aufsafz gebotene Systematik der praparativen Anwendungen beriicksichtigt vorwiegend neuere Ergebnisse. Im spater erscheinenden zweiten Teil des Beitrags werden die mechanistischen Aspekte der Diels-Alder-Reaktionen diskutiert. A) Definition und Entdeckungsgeschichte B) Die Dienkomponente 1. Offenkettige Diene 2. Offenkettige Diene mit Heteroatomen 3. Polyene 4. 1,2-Bisrnethylencycloalkane 5. Alicyclische Diene 6. Cyclopentadienone 7. o-Chinone und o-chinoide Systeme 8. Aromaten 9. Heterocyclen 10. Olefine und nichtkonjugierte Diene C ) Die Dienophilkomponente 1. Offenkettige Alkene und Alkine 2. Allene 3. Cyclische Dienophile 4. Cyclische Azoverbindungen 5. Weitere Pienophile mit Heteroatomen I , D) Retro-Diels-Alder-Reaktionen E) Ausblick A) Definition und Entdeckungsgeschichte Die Vereinigung konjugierter Diene mit Olefinen ist nur ein spezieller Fall des allgemeineren Reaktionsschemas der Cycloadditionen [I]; auf Kosten zweier Tc-Bindungen werden bei der Bildung des sechsgliedrigen Rings (1) zwei neue o-Bindungen gekniipft. Als weitere Beispiele fur Cycloadditionen sind Epoxydationen und Carbenadditionen, Dimerisierungen von Olefinen zu Cyclobutan-Derivaten sowie 1,3-Dipolare Additionsreaktionen zu nennen I* 921. Einzelne Beispiele fur Dienadditionen nach dern Diels-Alder-Schema frnden sich bereits in der Literatur der Jahrhundertwende. Wahrend Zincke [31 die bei der Pyrolyse von 1-Hydroxy-perchlorcyclopent-3-encarbonsaure beobachtete Dimerisation des intermediar auftretenden Tetrachlor-cyclopentadienons zu Perchlotindenon (2) richtig deutete, gelang die Strukturaufklarung fiir das 1 : I-Addukt (3) aus p-Benzochinon und Cyclopentadien erst Diels und Alder [41; fruhere Strukturvorschlage von Staudinger (mit Cyclobutan-Struktur) und Albrecht enviesen sich als revisionsbediirftig. (3) H O Die Struktur der 1 : 1-Additionsverbindung (4) aus Cyclopentadien und Azodicarbonsaureester [51 deutete erstmals an, daD es sich bei diesen Additionsreaktionen der r 1

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Dien‐Synthesen des 2.3‐Dihydro‐naphthalins und des Naphthalins mit N‐Phenyl‐maleinimid

Cited by 16 publications

References 9 publications

Perfluorobicyclo[2.2.0]hex-1(4)-ene as unique partner for Diels–Alder reactions with benzene: a density functional theory study

Perfluorobicyclo[2.2.0]hex-1(4)-ene as unique partner for Diels–Alder reactions with benzene: a density functional theory study

Synthesis of New Diphosphine Ligands and their Application in Pd‐Catalyzed Alkoxycarbonylation Reactions

Diels‐Alder‐Reaktionen I: Präparative Aspekte

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