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

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

Research output: Contribution to journalArticlepeer-review

38 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 languageEnglish (US)
Pages (from-to)4578-4581
Number of pages4
JournalOrganic Letters
Volume16
Issue number17
DOIs
StatePublished - Sep 5 2014

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

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