title: 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.
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Brian P
authors.initials: BP
authors.lastname: Woods
authors.forename: Beeraiah
authors.initials: B
authors.lastname: Baire
authors.forename: Thomas R
authors.initials: TR
authors.lastname: Hoye
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D061565:Cycloaddition Reaction; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000480:Alkynes; D006576:Heterocyclic Compounds, 4 or More Rings