The Diels-Alder Reaction of Anthracene with Nitroölefins. A New Route to 11-Nitro- and 11-Amino-9,10-dihydro-9,10-ethanoanthracenes<sup>1</sup>

Noland, Wayl­and E.; Freeman, Howard I.; Baker, M. Scott

doi:10.1021/ja01582a053

Cited by 22 publications

(9 citation statements)

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“…53 The reaction of anthracene with 1-nitronaphthalene at 3008C for 10 -15 h followed by aromatisation via loss of nitrous acid has also been reported, 54 and the yields of these reactions were found to be strongly affected by polymerisation of the nitroolefins. 55 Subsequent catalytic hydrogenation or reduction was used to produce the corresponding amines in this study.…”

Section: Additions To Anthracenementioning

confidence: 99%

Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

2003

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Section: Additions To Anthracenementioning

confidence: 99%

Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

2003

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“…This compound was prepared by the sequence recomnlended by Noland (27). The product was a laclirymator~~ yellow liquid, b.11.…”

Section: Nitroethylenementioning

confidence: 99%

Chemical Shifts in the N.M.R. Spectra of Substituted Xylenes

Fraser¹

1960

Can. J. Chem.

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The complete results of analysis of the N.M.R. spectra of twelve 2,6-dimethyl-1-substituted benzenes are reported. The results are interpreted as evidence that the ability of the substituent to donate or withdraw electrons by resonance interaction with the benzene ring is a major factor in determining the position of absorption of the protons attached to the ring. The chemical shifts and coupling constants for nitroethylene are also reported.

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“…Thus, under normal circumstances, nitroethylene does not behave as a masked acetylene. [16] Scheme 1. One-step conversion of aromatic hydrocarbon bay regions into new unsubstituted benzene rings by nitroethylene, generated in situ from 2-nitroethanol by dehydration with phthalic anhydride.…”

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confidence: 99%

One‐Step Conversion of Aromatic Hydrocarbon Bay Regions into Unsubstituted Benzene Rings: A Reagent for the Low‐Temperature, Metal‐Free Growth of Single‐Chirality Carbon Nanotubes

2010

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A tube ride: The controlled chemical synthesis of uniform, single‐walled carbon nanotubes from short hydrocarbon templates, such as aromatic belts and geodesic nanotube end‐caps, by a Diels–Alder cycloaddition/rearomatization strategy requires a potent “masked acetylene” capable of transforming hydrocarbon bay regions into new unsubstituted benzene rings in a single operation. Nitroethylene has been found to effect such benzannulations (see scheme).

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The Diels-Alder Reaction of Anthracene with Nitroölefins. A New Route to 11-Nitro- and 11-Amino-9,10-dihydro-9,10-ethanoanthracenes¹

Cited by 22 publications

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Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

Chemical Shifts in the N.M.R. Spectra of Substituted Xylenes

One‐Step Conversion of Aromatic Hydrocarbon Bay Regions into Unsubstituted Benzene Rings: A Reagent for the Low‐Temperature, Metal‐Free Growth of Single‐Chirality Carbon Nanotubes

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The Diels-Alder Reaction of Anthracene with Nitroölefins. A New Route to 11-Nitro- and 11-Amino-9,10-dihydro-9,10-ethanoanthracenes1

Cited by 22 publications

References 0 publications

Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

Chemical Shifts in the N.M.R. Spectra of Substituted Xylenes

One‐Step Conversion of Aromatic Hydrocarbon Bay Regions into Unsubstituted Benzene Rings: A Reagent for the Low‐Temperature, Metal‐Free Growth of Single‐Chirality Carbon Nanotubes

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The Diels-Alder Reaction of Anthracene with Nitroölefins. A New Route to 11-Nitro- and 11-Amino-9,10-dihydro-9,10-ethanoanthracenes¹