Cyclononatetraenide. A Ten-π-Electron Aromatic System

LaLancette, E. A.; Benson, R. E.

doi:10.1021/ja01087a018

Cited by 97 publications

(33 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A recent modification of this procedure has been described in which the dianion is generated with sodium in liquid ammonia. The order of reactivity CC1 4 > CHCI3 > CH 2 C1 2 indicates that the reaction is not a simple nucleo philic substitution, and the predominance of one isomer in these reactions, 43 although originally overestimated in the case of 9-chloro[6.1.0]bicyclononatriene, 44 also supports this view. The order of reactivity CC1 4 > CHCI3 > CH 2 C1 2 indicates that the reaction is not a simple nucleo philic substitution, and the predominance of one isomer in these reactions, 43 although originally overestimated in the case of 9-chloro[6.1.0]bicyclononatriene, 44 also supports this view.…”

Section: Monocyclic Systems With Ten ^-Electronsmentioning

confidence: 80%

“…59 The hyperfine pattern of nine main lines of binomial intensity, each split into a partially resolved multiplet, was consistent with a system of two sets of eight equivalent protons. 41 ' 43 Sodium cyclononatetraenide (19c) was prepared in lower yield by proton abstraction from bicyclo [6.1.0]nonatriene (61a) with the methyl sulfinyl carbanion in DMSO, 44 and less readily with other bases (Fig. 41 and 0.0 gauss), and can be assigned to the two sets of protons at positions 2 and 1, respectively.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Monocyclic and Polycyclic Aromatic Ions Containing Six or More π-Electrons

Garratt¹,

Sargent²

1971

Organic Chemistry: A Series of Monographs

View full text Add to dashboard Cite

Section: Monocyclic Systems With Ten ^-Electronsmentioning

confidence: 80%

mentioning

confidence: 99%

Monocyclic and Polycyclic Aromatic Ions Containing Six or More π-Electrons

Garratt¹,

Sargent²

1971

Organic Chemistry: A Series of Monographs

View full text Add to dashboard Cite

“…L'accord entre le resultat thtorique et I'expCrience constitue donc dans ce cas, un test de la validit6 de la mCthode MNDO dans le domaine des composCs soufres insaturks. Signalons enfin, que aprbs optimisation complbte de la gComCtrie, la mCthode MNDO indique que les cycles de tous les composCs pentagonaux monocycliques pris en conc-c (C3C4): [3,4].…”

Section: Methodesunclassified

Etude MNDO des composes conjugues enneagonaux

Ouamerali

Gayoso

1986

Int J of Quantum Chemistry

View full text Add to dashboard Cite

ResumeSelon les r6sultat.s obtenus au moyen de MNDO, apds optimisation complkte de la gkomktrie, les anions cyclononatetrwnyle et benzocyclononatetranyle, l'ennkapyrrole et I'enneathiophkne sont des composks plans a tendance aromatique. L'enneafulvkne posskde une conformation pkferentielle plane mais une structure de composk conjugut polybnique alors que I'enneafuranne et le cyclononatetraene sont des molkcules gauches. La methode de Huckel universelle (MHU), qui est une technique emphique simple, tenant compte de tous les klectrons de valence et decrivant les systkmes u au moyen d'oM localis6es, conduit aux m h e s conclusions que la mkthode MNDO. Les calculs effectuks au moyen de MNDO et MHU nous ont permis de d6crire I'ensemble des propri6tks physicochimiques des composks conjuguks enneagonawt pris en considkration.A notre connaissance, nous prksentons ici, la premikre etude tkhrique des composks conjuguks contenant le cycle k neuf membres. AbstractWe present MNLKI calculations of a series of nine-membered conjugated compounds. The geometries have been fully optimized. Cyclononatetraenyl and benzocyclononatetraenyl anions, nonapyrrol, and nonathiophene appear to be planar aromatic compounds. Following MNDO, nonafulvene has a planar prefeted conformation, but a polyenic structure, while nonafuran and cyclononatetraene are gauche molecules. The Universal Huckel Method (UHM), a simple all valence electron empirical technique which describes u systems using localized MO, gives, qualitatively, the same results as the MNDO method. The quantum calculation carried out with MNDO and UHM have been used to describe the physicochemical properties of ninemembered ring conjugated compounds under consideration. To our knowledge, we present here the f i t theoretical study dealing with nine-membered conjugated molecules.

show abstract

“…2) enthalt ausser dem Signal einer Acetylgruppe bei 1,98 ppm und dem komplexen Multiplett der aromatischen Protonen zwischen 7,9 und 6,4 ppm das Singulett einer -CH2-OAc-Gruppe bei 4,27 ppm. Die die beiden Fluorenringe verkniipfende CH,-Gruppe koppelt mit H-C (9'); das A ,BSystem absorbiert bei 2,80 und 3,20 (285) 87 (2), 78 (7), 77 (71, 320 (2510) 403 (175) sh 76 (6), 75 (7), 74 (61, 339 (810) 417 (61) 64 (lo), 63 (13), 62 (3), 345 (830) 428 (27) 352(790) 438 (4) (14) 205 (14). 204 ( M + , 86).…”

Section: 986unclassified

“…alkyl-acetate [I31 [I] auf Benzofulvene und Dibenzofulvene iibertragen lasse: Da abgeschatzt worden war, dass der pK,-Wert von Cyclononatetraen zwischen demjenigen von Cy~lopentadien~) und Inden liege [14], konnte das Verhalten von Acetoxymethylindenen (4) wertvolle Hinweise auf die Reaktivitat (und insbesondere die Eliminierungsbedingungen) von Acetoxymethyl-cyclononatetraen geben. Anderseits sollte ein thermischer disrotatorischer Ringschluss von Nonafulven zu 1,2-Dihydro-I, 2-benzofulven, oxydative Aromatisierung zu 1, fuhren, so dass auch die spektroskopischen Eigenschaften des bisher nur wenig charakterisierten Grundkorpers 6a interessierten.…”

unclassified

Synthese von Benzofulvenen und Dibenzofulvenen über 1‐Chloralkyl‐acetate

Neuenschwander¹,

Vögeli²,

Fahrni³

et al. 1977

Helvetica Chimica Acta

View full text Add to dashboard Cite

(7.11.77) Synthesis of benzofulvenes and dibenzofulvenes via 1-chloroalkyl-acetates Summary 1,2-Benzofulvene (6a) and 1,2,3,4-dibenzofulvene (7a) as well as the corresponding 6-methyl-and 6-phenyl-derivatives are prepared by reaction of sodium indenide and sodium fluorenide with l-chloroalkyl acetates (3), followed by elimination with KOC (CH,),. The over-all yields are comparable with the results of the fulvene series and are in most cases considerably higher than the yields of the Thiele-method. Im Rahmen von Versuchen zur Herstellung von Nonafulven [I21 stellte sich die Frage, ob sich die von uns entwickelte Synthese von Fulvenen iiber l-Chlor-

show abstract

Cyclononatetraenide. A Ten-π-Electron Aromatic System

Cited by 97 publications

References 3 publications

Monocyclic and Polycyclic Aromatic Ions Containing Six or More π-Electrons

Monocyclic and Polycyclic Aromatic Ions Containing Six or More π-Electrons

Etude MNDO des composes conjugues enneagonaux

Synthese von Benzofulvenen und Dibenzofulvenen über 1‐Chloralkyl‐acetate

Contact Info

Product

Resources

About