Intramolecular Capture of HDDA-Derived Benzynes: (I) 6- to 12-Membered Ring Formation, (II) Internally (vis-à-vis Remotely) Tethered Traps, and (III) Role of the Rate of Trapping by the Benzynophile

Yuanxian Wang, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Reported here are studies that have established novel features of the hexadehydro-Diels-Alder reaction of substrates containing tethered trapping moieties. Products having new structural motifs can be created. (i) Medium-sized fused rings can be produced by varying the length of the tether. (ii) The tether can emanate from an atom within the linker unit that joins the 1,3-diyne and diynophile. (iii) The importance of the rate of trapping by the benzynophile is established. [Figure Presented]

Original languageEnglish (US)
Pages (from-to)88-91
Number of pages4
JournalOrganic Letters
Volume20
Issue number1
DOIs
StatePublished - Jan 5 2018

Bibliographical note

Funding Information:
Support for this research was provided by the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (GM65597) and the Chemistry Division of the National Science Foundation (CHE1665389). Some of the NMR spectral data were acquired with an instrument acquired with funds provided by the NIH Shared Instrumentation Grant program (S10OD011952). Dr. Victor G. Young (University of Minnesota) is acknowledged for performing the X-ray diffraction analysis.

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