Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure

[Image: see text] The rates of the hexadehydro-Diels–Alder (HDDA) reaction of substrates containing, minimally, a 1,3,8-triyne subunit are reported. Several series of related substrates, differing in the nature of the three-atom tether that links the 1,3-diyne and diynophile, were examined. Seemingl...

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Autores principales: Woods, Brian P., Baire, Beeraiah, Hoye, Thomas R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156263/
https://www.ncbi.nlm.nih.gov/pubmed/25153729
http://dx.doi.org/10.1021/ol502131r
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author Woods, Brian P.
Baire, Beeraiah
Hoye, Thomas R.
author_facet Woods, Brian P.
Baire, Beeraiah
Hoye, Thomas R.
author_sort Woods, Brian P.
collection PubMed
description [Image: see text] The rates of the hexadehydro-Diels–Alder (HDDA) reaction of substrates containing, minimally, a 1,3,8-triyne subunit are reported. Several series of related substrates, differing in the nature of the three-atom tether that links the 1,3-diyne and diynophile, were examined. Seemingly small changes in substrate structure result in large differences in cyclization rate, spanning more than 8 orders of magnitude. The reactivity trends revealed by these studies should prove useful in guiding substrate design and choice of reaction conditions in future applications.
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spelling pubmed-41562632015-08-25 Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure Woods, Brian P. Baire, Beeraiah Hoye, Thomas R. Org Lett [Image: see text] The rates of the hexadehydro-Diels–Alder (HDDA) reaction of substrates containing, minimally, a 1,3,8-triyne subunit are reported. Several series of related substrates, differing in the nature of the three-atom tether that links the 1,3-diyne and diynophile, were examined. Seemingly small changes in substrate structure result in large differences in cyclization rate, spanning more than 8 orders of magnitude. The reactivity trends revealed by these studies should prove useful in guiding substrate design and choice of reaction conditions in future applications. American Chemical Society 2014-08-25 2014-09-05 /pmc/articles/PMC4156263/ /pubmed/25153729 http://dx.doi.org/10.1021/ol502131r Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Woods, Brian P.
Baire, Beeraiah
Hoye, Thomas R.
Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure
title Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure
title_full Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure
title_fullStr Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure
title_full_unstemmed Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure
title_short Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure
title_sort rates of hexadehydro-diels–alder (hdda) cyclizations: impact of the linker structure
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156263/
https://www.ncbi.nlm.nih.gov/pubmed/25153729
http://dx.doi.org/10.1021/ol502131r
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