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Efficient phenanthrene, helicene, and azahelicene syntheses

Efficient phenanthrene, helicene, and azahelicene syntheses
Efficient phenanthrene, helicene, and azahelicene syntheses
Homolytic aromatic substitution reactions are used for the efficient regioselective synthesis of helicenes, phenanthrenes, and azahelicenes. The use of halo and alkoxy substituents to control the stereochemical outcome of this approach and X-ray studies of the resulting helicenes are described (see structure; red O, gray C).
helicenes, homolytic aromatic substitution, polyaromatic compounds, protecting groups, radical cyclization intramolecular radical additions, chiral discrimination, asymmetric-synthesis, molecular-structure, circular-dichroism, wittig reaction, anion-radicals, photocyclization, quinolines, catalysis
1433-7851
2242-2245
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Guy, Ian L.
b7d1bed5-2418-43d4-bb05-1db8d1bcc2db
Nanson, Lana
45d26fc2-88f6-484a-9436-874e0c7f4d4d
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Guy, Ian L.
b7d1bed5-2418-43d4-bb05-1db8d1bcc2db
Nanson, Lana
45d26fc2-88f6-484a-9436-874e0c7f4d4d

Harrowven, David C., Guy, Ian L. and Nanson, Lana (2006) Efficient phenanthrene, helicene, and azahelicene syntheses. Angewandte Chemie International Edition, 45 (14), 2242-2245. (doi:10.1002/anie.200504287). (PMID:16506249)

Record type: Article

Abstract

Homolytic aromatic substitution reactions are used for the efficient regioselective synthesis of helicenes, phenanthrenes, and azahelicenes. The use of halo and alkoxy substituents to control the stereochemical outcome of this approach and X-ray studies of the resulting helicenes are described (see structure; red O, gray C).

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More information

Published date: 2006
Additional Information: Communication
Keywords: helicenes, homolytic aromatic substitution, polyaromatic compounds, protecting groups, radical cyclization intramolecular radical additions, chiral discrimination, asymmetric-synthesis, molecular-structure, circular-dichroism, wittig reaction, anion-radicals, photocyclization, quinolines, catalysis

Identifiers

Local EPrints ID: 44459
URI: http://eprints.soton.ac.uk/id/eprint/44459
ISSN: 1433-7851
PURE UUID: 8239928c-46a0-4a02-aa97-6afc3b0185cf
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

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Date deposited: 05 Mar 2007
Last modified: 16 Mar 2024 02:46

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Contributors

Author: Ian L. Guy
Author: Lana Nanson

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