A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions

Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the forma...

Descripción completa

Detalles Bibliográficos
Autores principales: Debeaux, Marc, Brandhorst, Kai, Jones, Peter G, Hopf, Henning, Grunenberg, Jörg, Kowalsky, Wolfgang, Johannes, Hans-Hermann
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2009
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2707016/
https://www.ncbi.nlm.nih.gov/pubmed/19597557
http://dx.doi.org/10.3762/bjoc.5.31
_version_ 1782169124243243008
author Debeaux, Marc
Brandhorst, Kai
Jones, Peter G
Hopf, Henning
Grunenberg, Jörg
Kowalsky, Wolfgang
Johannes, Hans-Hermann
author_facet Debeaux, Marc
Brandhorst, Kai
Jones, Peter G
Hopf, Henning
Grunenberg, Jörg
Kowalsky, Wolfgang
Johannes, Hans-Hermann
author_sort Debeaux, Marc
collection PubMed
description Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the formation of 7 and the hydrogenated compound 13 is observed. A mechanism for the formation of the reaction products is proposed and supported by DFT calculations.
format Text
id pubmed-2707016
institution National Center for Biotechnology Information
language English
publishDate 2009
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-27070162009-07-13 A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions Debeaux, Marc Brandhorst, Kai Jones, Peter G Hopf, Henning Grunenberg, Jörg Kowalsky, Wolfgang Johannes, Hans-Hermann Beilstein J Org Chem Full Research Paper Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the formation of 7 and the hydrogenated compound 13 is observed. A mechanism for the formation of the reaction products is proposed and supported by DFT calculations. Beilstein-Institut 2009-06-16 /pmc/articles/PMC2707016/ /pubmed/19597557 http://dx.doi.org/10.3762/bjoc.5.31 Text en Copyright © 2009, Debeaux et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Debeaux, Marc
Brandhorst, Kai
Jones, Peter G
Hopf, Henning
Grunenberg, Jörg
Kowalsky, Wolfgang
Johannes, Hans-Hermann
A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions
title A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions
title_full A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions
title_fullStr A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions
title_full_unstemmed A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions
title_short A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions
title_sort stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2707016/
https://www.ncbi.nlm.nih.gov/pubmed/19597557
http://dx.doi.org/10.3762/bjoc.5.31
work_keys_str_mv AT debeauxmarc astableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT brandhorstkai astableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT jonespeterg astableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT hopfhenning astableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT grunenbergjorg astableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT kowalskywolfgang astableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT johanneshanshermann astableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT debeauxmarc stableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT brandhorstkai stableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT jonespeterg stableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT hopfhenning stableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT grunenbergjorg stableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT kowalskywolfgang stableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions
AT johanneshanshermann stableenolfroma6substitutedbenzanthroneanditsunexpectedbehaviourunderacidicconditions

Ejemplares similares