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

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.

SUBMITTER: Woods BP

PROVIDER: S-EPMC4156263 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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

Woods Brian P BP Baire Beeraiah B Hoye Thomas R TR

Organic letters 20140825 17

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 ...[more]

PMID: 25153729

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