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

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

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

Author(s) -

Brian P. Woods,

Beeraiah Baire,

Thomas R. Hoye

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502131r

Subject(s) - chemistry , linker , reactivity (psychology) , substrate (aquarium) , diels–alder reaction , protein subunit , stereochemistry , computational chemistry , organic chemistry , catalysis , biochemistry , ecology , medicine , alternative medicine , pathology , computer science , gene , biology , operating system

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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