Rates of hexadehydro-Diels-Alder (HDDA) cyclizations: Impact of the linker structure

Brian P. Woods; Beeraiah Baire; Thomas R. Hoye

doi:10.1021/ol502131r

Rates of hexadehydro-Diels-Alder (HDDA) cyclizations: Impact of the linker structure

Brian P. Woods, Beeraiah Baire, Thomas R. Hoye

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

49 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	4578-4581
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	17
DOIs	https://doi.org/10.1021/ol502131r
State	Published - Sep 5 2014

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© 2014 American Chemical Society.

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AB - 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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Rates of hexadehydro-Diels-Alder (HDDA) cyclizations: Impact of the linker structure

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