The Molecular Structure of 3-Methylene-1,4-pentadiene Studied by Gas-Phase Electron Diffraction and by Vibrational, NMR and Ultraviolet Spectroscopy.

Almenningen, A.; Gatial, A.; Grace, D. S. B.; Hopf, H.; Klæboe, P.; Lehrich, F.; Nielsen, Claus J.; Powell, D. L.; Trætteberg, M.

doi:10.3891/acta.chem.scand.42a-0634

Cited by 33 publications

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“…. [26] investigations on [3]dendralene (11) [181,182] and [4]dendralene (21). [183,184] In all other respects, the dendralenes exhibit IR and NMR spectroscopic and mass spectrometric data as expected, and the reader is referred to the original literature [23,26] for specific information.…”

Section: Spectroscopic and Structural Propertiesmentioning

confidence: 75%

Dendralenes Branch Out: Cross‐Conjugated Oligoenes Allow the Rapid Generation of Molecular Complexity

2012

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Twenty-seven years ago, H. Hopf published the only previous comprehensive review on branched oligoenes that had the title "Dendralenes: A Neglected Family of Hydrocarbons". The dendralenes are no longer neglected. Research into the synthesis, properties, and applications of dendralenes is rapidly gaining momentum and this Review summarizes important recent findings. From significant fundamental properties (the first demonstration of alternating behavior since the annulenes) through to unparalleled complexity-generating synthetic transformations, this fundamental oligoene family is coming of age. Effective synthetic approaches to cyclic and acyclic dendralene systems are analyzed and classified. The most powerful synthetic transformations of the dendralenes, diene-transmissive Diels-Alder reactions, are surveyed in detail.

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Section: Spectroscopic and Structural Propertiesmentioning

confidence: 75%

Dendralenes Branch Out: Cross‐Conjugated Oligoenes Allow the Rapid Generation of Molecular Complexity

2012

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“…It is further noteworthy that in the prevailing structure of the simplest crossconjugated compound, [3]dendralene (3-methylenepenta-1,4-diene), there is a slightly twisted anti-butadiene fragment while the third vinyl group is rotated by 40-50°rela-tive to the butadiene plane. [29,30] By exhibiting small dihedral angles θ around the phenylbutadiene essential single bonds, the solid state geometry suggests that occurrence of conjugation in the styrene parts is more important than conjugation in the butadiene fragment. The ab initio calculations refine this picture and show that butadiene conjugation can certainly not be neglected.…”

Section: General Discussion and Conclusionmentioning

confidence: 99%

On the Structure of Cross‐Conjugated 2,3‐Diphenylbutadiene

Walree¹,

Wiel²,

Jenneskens³

et al. 2007

Eur J Org Chem

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The structure of the cross-conjugated compound 2,3-diphenylbutadiene was investigated by single-crystal X-ray diffraction and computational methods. In the crystal structure the central butadiene fragment adopts an s-gauche geometry [-55.6(2)°torsion angle φ around the essential single bond], whereas the styrene moieties are close to planarity. MP2/6-311G* calculations show that the s-gauche conformation represents the global minimum along the φ coordinate, but also revealed the existence of an s-trans local minimum.

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“…Im Unterschied hierzu haben die Konformationsminima der ungeradzahligen Reihe mindestens eine quasi-s-cis-Einheit (Abbildung 4 a). Die berechneten Geometrien stimmen sehr gut mit experimentellen Daten aus Elektronenbeugungsuntersuchungen an 11 [181,182] und 21 [183,184] überein.…”

Section: Spektroskopische Und Strukturelle Eigenschaftenunclassified

Dendralene auf dem Vormarsch: kreuzkonjugierte Oligoene ermöglichen den schnellen Aufbau molekularer Komplexität

Hopf

Sherburn

2012

Angewandte Chemie

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Vor 27 Jahren veröffentlichte H. Hopf den bisher einzigen umfassenden Übersichtsartikel zu verzweigten Oligoenen mit dem Titel “Dendralene – eine vernachlässigte Gruppe hochungesättigter Kohlenwasserstoffe”. Die Dendralene werden heutzutage nicht mehr vernachlässigt. Die Forschung zu Synthese, Eigenschaften und Anwendungen der Dendralene hat in jüngster Zeit viele neue Impulse erhalten, und der vorliegende Aufsatz fasst die bedeutenden Ergebnisse der letzten Jahre zusammen. Von grundlegend wichtigen Eigenschaften (der ersten Demonstration von alternierendem Verhalten seit den Annulenen) bis zu unvergleichbaren, molekulare Komplexität erzeugenden, chemischen Transformationen: Die als Dendralene bekannte Klasse der Oligoene ist erwachsen geworden! Die verschiedenen Synthesewege zu acyclischen und cyclischen Dendralenen werden analysiert und klassifiziert. Die leistungsfähigste Umwandlung der Dendralene – die Dien‐transmissive Diels‐Alder‐Reaktion (DTDA‐Reaktion) – wird in einer detaillierten Übersicht vorgestellt.

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The Molecular Structure of 3-Methylene-1,4-pentadiene Studied by Gas-Phase Electron Diffraction and by Vibrational, NMR and Ultraviolet Spectroscopy.

Cited by 33 publications

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Dendralenes Branch Out: Cross‐Conjugated Oligoenes Allow the Rapid Generation of Molecular Complexity

Dendralenes Branch Out: Cross‐Conjugated Oligoenes Allow the Rapid Generation of Molecular Complexity

On the Structure of Cross‐Conjugated 2,3‐Diphenylbutadiene

Dendralene auf dem Vormarsch: kreuzkonjugierte Oligoene ermöglichen den schnellen Aufbau molekularer Komplexität

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