Selenium halide-induced bridge formation in [2.2]paracyclophanes

An addition/elimination sequence of selenium halides to pseudo-geminally bis(acetylene) substituted [2.2]paracyclophanes leads to new bridges with an endo-exo-diene substructure. The reactions have been found to be sensitive to the substitution of the ethynyl group. The formation of dienes with a zi...

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Detalles Bibliográficos
Autores principales: Sarbu, Laura G, Hopf, Henning, Jones, Peter G, Birsa, Lucian M
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4222412/
https://www.ncbi.nlm.nih.gov/pubmed/25383126
http://dx.doi.org/10.3762/bjoc.10.266
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author Sarbu, Laura G
Hopf, Henning
Jones, Peter G
Birsa, Lucian M
author_facet Sarbu, Laura G
Hopf, Henning
Jones, Peter G
Birsa, Lucian M
author_sort Sarbu, Laura G
collection PubMed
description An addition/elimination sequence of selenium halides to pseudo-geminally bis(acetylene) substituted [2.2]paracyclophanes leads to new bridges with an endo-exo-diene substructure. The reactions have been found to be sensitive to the substitution of the ethynyl group. The formation of dienes with a zig-zag configuration is related to that observed for non-conjugated cyclic diynes of medium ring size.
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spelling pubmed-42224122014-11-07 Selenium halide-induced bridge formation in [2.2]paracyclophanes Sarbu, Laura G Hopf, Henning Jones, Peter G Birsa, Lucian M Beilstein J Org Chem Full Research Paper An addition/elimination sequence of selenium halides to pseudo-geminally bis(acetylene) substituted [2.2]paracyclophanes leads to new bridges with an endo-exo-diene substructure. The reactions have been found to be sensitive to the substitution of the ethynyl group. The formation of dienes with a zig-zag configuration is related to that observed for non-conjugated cyclic diynes of medium ring size. Beilstein-Institut 2014-10-31 /pmc/articles/PMC4222412/ /pubmed/25383126 http://dx.doi.org/10.3762/bjoc.10.266 Text en Copyright © 2014, Sarbu 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
Sarbu, Laura G
Hopf, Henning
Jones, Peter G
Birsa, Lucian M
Selenium halide-induced bridge formation in [2.2]paracyclophanes
title Selenium halide-induced bridge formation in [2.2]paracyclophanes
title_full Selenium halide-induced bridge formation in [2.2]paracyclophanes
title_fullStr Selenium halide-induced bridge formation in [2.2]paracyclophanes
title_full_unstemmed Selenium halide-induced bridge formation in [2.2]paracyclophanes
title_short Selenium halide-induced bridge formation in [2.2]paracyclophanes
title_sort selenium halide-induced bridge formation in [2.2]paracyclophanes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4222412/
https://www.ncbi.nlm.nih.gov/pubmed/25383126
http://dx.doi.org/10.3762/bjoc.10.266
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AT hopfhenning seleniumhalideinducedbridgeformationin22paracyclophanes
AT jonespeterg seleniumhalideinducedbridgeformationin22paracyclophanes
AT birsalucianm seleniumhalideinducedbridgeformationin22paracyclophanes

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