The reaction of benzonorbornadiene and related compounds with iron carbonyls

Lombardo, Louis J.; Wege, Dieter; Wilkinson, S. P.

doi:10.1071/ch9740143

Cited by 33 publications

(22 citation statements)

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“…The parent benzyne, generated in situ from benzenediazonium-2-carboxylate ( 10 ) under mild thermal conditions, was reported to react with 2,5-diphenylfuran to form 1,4-dihydro-1,4-diphenyl-1,4-epoxynaphthalene as the Diels–Alder adduct . Other benzynes were also reported to undergo the Diels–Alder reactions with 2,5-diphenylfuran to form 1,4-epoxynaphthalenes. , Hydrogenation of the carbon–carbon double bond in 1,4-epoxynaphthalenes followed by elimination of the oxygen bridges could then produce the corresponding 1,4-diphenylnaphthalenes. , Alternatively, reductive deoxygenation with Fe 2 (CO) 9 could also lead to 1,4-diphenylnaphthalenes . We used 10 to generate in situ the parent benzyne for the Diels–Alder reactions with the two 2,5-diphenylfuran units in syn - 9 and anti - 9 .…”

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Synthesis and Characterization of Functionalized [12]Cycloparaphenylenes Containing Four Alternating Biphenyl and Naphthyl Units

et al. 2017

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Functionalized [12]cycloparaphenylenes ([12]CPPs) containing four alternating biphenyl and naphthyl units were synthesized. A macrocyclic furan-containing CPP precursor was used for the Diels-Alder reaction with the parent benzyne or 3,6-dimethoxybenzyne to form the corresponding macrocyclic carbon frameworks. The subsequent reductive deoxygenation of the Diels-Alder adducts with Fe(CO) followed by oxidative aromatization with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone produced the functionalized [12]CPPs. The effect of macrocyclic ring size on the reaction rate of oxidative aromatization was investigated.

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confidence: 99%

Synthesis and Characterization of Functionalized [12]Cycloparaphenylenes Containing Four Alternating Biphenyl and Naphthyl Units

et al. 2017

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“…A [4 + 2] cycloaddition reaction of the furan derivative 9 with the benzonorbornadiene derivative 10 which afforded the adduct 11 in 72% yield (Scheme 2) [22,23]. The C s symmetrical geometry of 11 was verified by the presence of 14 absorption signals in the 13 C NMR spectrum.…”

Section: Unsymmetrical Pentacene-co Adductmentioning

confidence: 99%

Soluble pentacene precursors: strategic design, synthesis, and characterization

Chow¹,

Chuang²,

Huang³

et al. 2008

SPIE Proceedings

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“…An der Doppelbindung der Seitenkette sind jedoch diesmal funktionelle Gruppe und Norbornenyleinheit trans-standig angeordnet. Schema 5 9 10…”

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Eisenpentacarbonyl‐induzierte Reaktionen von Norbornadien und substituierten Olefinen

Schmid

Naab

Hayakawa

1978

Helvetica Chimica Acta

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The photochemical reaction of norbornadiene and a,a-unsaturated nitriles, esters and amides in the presence of Fe(CO)S was studied. Nitriles furnished the dinorbornenyl ketones 2a-c (Scheme 1). Esters led to an addition of a norbornene moiety to the double bond giving the substituted a,P-unsaturated esters 10a and 10b (Scheme 5). Methacrylamide and methyl p-aminocrotonate gave the cyclopentanone derivatives 14 and 17, respectively (Schemes 7 and 8). The reaction was in all cases highly stereoselective with general exo-substitution on the norbornadiene. The attack on the unsymmetric olefins occurred regiospecifically at that point of the double bond which was furthest away from the functional group. A plausible mechanism for these reactions is suggested in Schemes 10 and 11.Eisencarbonyl-induzierte Kupplungs-und Carbonylierungsreaktionen von Olefinen besitzen aufgrund ihres stereospezifischen Verlaufs grosses Interesse. Die Umsetzung von gespannten bicyclischen Systemen vom Norbornen-bzw. Norbornadientyp fiihrte dabei zu symmetrischen Cyclopentanonen in teilweise ausgezeichneten praparativen Ausbeuten [ 11. In der vorliegenden Arbeit wird uber die ((gemischte)) Reaktion von Norbornadien mit einfachen, nicht gespannten Olefinen in Gegenwart von Eisenpentacarbonyl berichtet (vgl. auch [2]): Die Umsetzung zweier strukturell verschiedener Olefine wurde untersucht, da es von Interesse war zu wissen, welches der vielen moglichen Kupplungsprodukte entsteht. Insbesondere galt es, die Frage zu beantworten, ob die Reaktion auch unter diesen Voraussetzungen zu Cyclopentanonen fuhrt. Ausserdem erhoffte man, so eine grossere strukturelle Vielfalt bei den Produkten zu erreichen.Als ein Reaktionspartner bot sich Norbornadien an, da zum einen Derivate dieses Bicyclus haufig wertvolle Ausgangsprodukte fur Synthesen darstellen, zum andern die Ringspannung dieses Olefins einen positiven Einfluss auf die Bildung von Kupplungsprodukten haben sollte'). Einfache, nicht gespannte Olefine wurden I)Weissberger et al.[la] berichten, dass nur die Verwendung von gespannten cyclischen Olefinen bei der Eisenpentacarbonyl-induzierten Kupplung zu guten Ausbeuten an organischem Material fiihrt.

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The reaction of benzonorbornadiene and related compounds with iron carbonyls

Cited by 33 publications

References 0 publications

Synthesis and Characterization of Functionalized [12]Cycloparaphenylenes Containing Four Alternating Biphenyl and Naphthyl Units

Synthesis and Characterization of Functionalized [12]Cycloparaphenylenes Containing Four Alternating Biphenyl and Naphthyl Units

Soluble pentacene precursors: strategic design, synthesis, and characterization

Eisenpentacarbonyl‐induzierte Reaktionen von Norbornadien und substituierten Olefinen

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