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Radical Stabilization Algorithm as a Predictive Tool for Novel and Reported Noncanonical Thiele’s Acid Analogues

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dc.contributor.author Chen, Jun
dc.contributor.author Lu, Lingxiao
dc.contributor.author Wulff, Jeremy E.
dc.date.accessioned 2020-06-21T13:34:38Z
dc.date.available 2020-06-21T13:34:38Z
dc.date.copyright 2017 en_US
dc.date.issued 2017
dc.identifier.citation Chen, J., Lu, L., & Wulff, J. E. (2017). Radical stabilization algorithm as a predictive tool for novel and reported noncanonical Thiele’s acid analogues. Synlett, 28(20), 2777- 2782. https://doi.org/10.1055/s-0036-1588583 en_US
dc.identifier.uri https://doi.org/10.1055/s-0036-1588583
dc.identifier.uri http://hdl.handle.net/1828/11869
dc.description.abstract We recently showed that a simple radical-stabilization algorithm outperformed traditional frontier-molecular orbital methods for rationalizing the outcome of the venerable Thiele’s acid (or ester) Diels–Alder dimerization. In the present Communication, we describe a novel noncanonical Thiele-type dimerization of a cyclopentadiene phosphine oxide, and show that when steric factors are taken into account the ­radical-stabilization method once again correctly rationalizes the regio­chemical outcome for the reaction. We further show that the method appears to be general for all known Thiele- and half-Thiele dimerization events. en_US
dc.description.sponsorship JW acknowledges salary support from the Canada Research Chairs program. en_US
dc.language.iso en en_US
dc.publisher Synlett en_US
dc.subject Diels-Alder reaction en_US
dc.subject Thiele's acid en_US
dc.subject predictive methods for cycloadditions en_US
dc.title Radical Stabilization Algorithm as a Predictive Tool for Novel and Reported Noncanonical Thiele’s Acid Analogues en_US
dc.type Article en_US
dc.description.scholarlevel Faculty en_US
dc.description.reviewstatus Reviewed en_US


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