Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols

Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisa...

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Autores principales: Abraham, Michael, Reischl, Wolfgang, Kirchner, Karl A., Roller, Alexander, Veiros, Luis F., Widhalm, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268543/
https://www.ncbi.nlm.nih.gov/pubmed/23222901
http://dx.doi.org/10.3390/molecules171214531
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author Abraham, Michael
Reischl, Wolfgang
Kirchner, Karl A.
Roller, Alexander
Veiros, Luis F.
Widhalm, Michael
author_facet Abraham, Michael
Reischl, Wolfgang
Kirchner, Karl A.
Roller, Alexander
Veiros, Luis F.
Widhalm, Michael
author_sort Abraham, Michael
collection PubMed
description Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided.
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spelling pubmed-62685432018-12-14 Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols Abraham, Michael Reischl, Wolfgang Kirchner, Karl A. Roller, Alexander Veiros, Luis F. Widhalm, Michael Molecules Article Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided. MDPI 2012-12-07 /pmc/articles/PMC6268543/ /pubmed/23222901 http://dx.doi.org/10.3390/molecules171214531 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Abraham, Michael
Reischl, Wolfgang
Kirchner, Karl A.
Roller, Alexander
Veiros, Luis F.
Widhalm, Michael
Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols
title Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols
title_full Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols
title_fullStr Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols
title_full_unstemmed Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols
title_short Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols
title_sort tandem rcm–claisen rearrangement–[2+2] cycloaddition of o,o'-(but-2-en-1,4-diyl)-bridged binaphthols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268543/
https://www.ncbi.nlm.nih.gov/pubmed/23222901
http://dx.doi.org/10.3390/molecules171214531
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