Competition between classical and hexadehydro-Diels-Alder (HDDA) reactions of HDDA triynes with furan We dedicate this Letter to the memory of Harry H. Wasserman, whose amalgamation of scholarship, artistry, and humanity stand as an admirable model for all to emulate

Quang Luu Nguyen, Beeraiah Baire, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

We report here thermal reactions between furan and one of three related triyne substrates. Each triyne is capable of reacting initially in two modes: (i) unimolecular hexadehydro-Diels-Alder (HDDA) reaction or (ii) bimolecular Diels-Alder reaction between one of its alkynes with furan. The relative rates of these initial events are such that two of the substrates react essentially in only one of modes (i) or (ii). The third is intermediate in behavior; its bifurcation is dependent on the concentration of the furan reactant. These results teach, more generally, principles relevant to the design of efficient HDDA-based reaction cascades.

Original languageEnglish (US)
Pages (from-to)3265-3267
Number of pages3
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - May 25 2015

Bibliographical note

Funding Information:
Financial support for this research was provided by the National Institutes of Health ( GM65597 and CA76497 ). Q.L.N. was supported by a Heisig/Gleysteen summer research fellowship for undergraduate students. The authors thank Brian P. Woods for helpful guidance, Laura J. Clouston and Victor G. Young, Jr. for assistance with the X-ray diffraction analysis, and Severin K. Thompson for collection of 13 C NMR data.

Keywords

  • Concentration dependence
  • HDDA-cascades
  • Homo-Diels-Alder
  • [2+2+2]-Cycloaddition

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