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A simple route to derivatives of benzo[j]fluoranthene

Tate, D.J., Abdelbasit, M., Kilner, C.A., Shepherd, H.J., Warriner, S.L., Bushby, R.J. (2014) A simple route to derivatives of benzo[j]fluoranthene. Tetrahedron, 70 (1). pp. 67-74. ISSN 00404020 (ISSN). (doi:10.1016/j.tet.2013.11.029) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided) (KAR id:50816)

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3,6,8,11-Tetramethoxybenzo[j]fluoranthene can be made from 1,6-dimethoxynaphthalene in a one-pot ferric chloride oxidation/methanol reduction procedure. The reaction is tolerant of the presence of substituents in the 7-position of the naphthalene nucleus and provides a quick and easy route to these particular benzo[j]fluoranthenes. The reactions presumably proceed through initial formation of a bond between the 4-positions of two naphthalene molecules followed by closure of the five-membered ring. Indeed in one case some 4,4�-binaphthyl was isolated from the reaction mixture and it was generally found that better yields of the benzo[j]fluoranthrenes were obtained starting from the 4,4�-binaphthyl rather than by using the naphthalene as the starting material. In an analogous manner to the ring-closure of the 4,4�-binaphthyls, starting from a hexakisalkoxyphenylnaphthalene, a hexakisalkoxyfluoranthene could be obtained. © 2013 Elsevier Ltd. All rights reserved.

Item Type: Article
DOI/Identification number: 10.1016/j.tet.2013.11.029
Additional information: Unmapped bibliographic data: LA - English [Field not mapped to EPrints] J2 - Tetrahedron [Field not mapped to EPrints] AD - School of Chemistry, University of Leeds, Woodhouse Lane, Leeds, LS2 9JT, United Kingdom [Field not mapped to EPrints] AD - Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, United Kingdom [Field not mapped to EPrints] DB - Scopus [Field not mapped to EPrints]
Uncontrolled keywords: Benzo[j]fluoranthene, Ferric chloride, Fluoranthene, Scholl reaction, 1 (3',4' bis(hexyloxy)phenyl) 2,3,6,7 tetrakis(hexyloxy) naphthalene, 1 bromo 2,3,6,7 tetrakis(hexyloxy)naphthalene, 1,2,5,6,8,9 hexakis(hexyloxy)fluoranthene, 1,6 dimethoxy 7 (4 methoxyphenyl)naphthalene, 1,6,7 trimethoxynaphthalene, 2 (4,7 dimethoxynaphthalen 1 yl) 4,4,5,5 tetramethyl[1,3,2]dioxaborolane, 2,3,6,7 tetrakis(hexyloxy)naphthalene, 2,3,6,7 tetramethoxynaphthalene, 3 chloro 1,2,5,6,8,9 hexakis(hexyloxy)fluoranthene, 3,5,6,8,10,11 hexamethoxybenzo[j]fluoranthene, 3,6 dibromo 2,7 dihydroxynaphthalene, 3,6 dibromo 2,7 dimethoxynaphthalene, 3,6,8,11 tetramethoxybenzo[j]fluoranthene, 4 iodo 1,6 dimethoxynaphthalene, 4,7,4',7' tetramethoxy[1,1']binaphthalenyl, 5,10 dibromo 3,6,8,11 tetramethoxybenzo[j]fluoranthene, 6,6 dibromo 4,4',7,7' tetramethoxy 1,1' binapthalene, 7 bromo 1,6 dimethoxynaphthalene, 7 iodo 1,6 dimethoxynaphthalene, benzo j fluoranthene derivative, ferric chloride, fluoranthene, methanol, naphthalene, unclassified drug, article, carbon nuclear magnetic resonance, drug structure, drug synthesis, oxidation reduction reaction, priority journal, proton nuclear magnetic resonance, thin layer chromatography
Subjects: Q Science > QD Chemistry > QD156 Inorganic synthesis
Divisions: Divisions > Division of Natural Sciences > Physics and Astronomy
Depositing User: Giles Tarver
Date Deposited: 21 Oct 2015 16:16 UTC
Last Modified: 17 Aug 2022 10:59 UTC
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