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

doi:10.1016/j.tetlet.2014.12.053

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

16 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 language	English (US)
Pages (from-to)	3265-3267
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2014.12.053
State	Published - 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.

Publisher Copyright:
© 2015 Elsevier Ltd.

Keywords

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

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Luu Nguyen, Q., Baire, B., & Hoye, T. R. (2015). 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. Tetrahedron Letters, 56(23), 3265-3267. https://doi.org/10.1016/j.tetlet.2014.12.053

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. / Luu Nguyen, Quang; Baire, Beeraiah; Hoye, Thomas R.
In: Tetrahedron Letters, Vol. 56, No. 23, 25.05.2015, p. 3265-3267.

Research output: Contribution to journal › Article › peer-review

Luu Nguyen, Q, Baire, B & Hoye, TR 2015, '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', Tetrahedron Letters, vol. 56, no. 23, pp. 3265-3267. https://doi.org/10.1016/j.tetlet.2014.12.053

Luu Nguyen Q, Baire B, Hoye TR. 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. Tetrahedron Letters. 2015 May 25;56(23):3265-3267. doi: 10.1016/j.tetlet.2014.12.053

Luu Nguyen, Quang ; Baire, Beeraiah ; Hoye, Thomas R. / 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. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 23. pp. 3265-3267.

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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

Abstract

Bibliographical note

Keywords

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