Isomerizations of Propargyl 3-Acylpropiolates via Reactive Allenes

Yuanxian Wang, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Thermal isomerizations of various propargyl 3-acylpropiolates are described. Many result in the formation of 3-acylbutenolides. These reactions appear to proceed through intermediate 2,3-dehydropyrans (strained cyclic allenes), which then isomerize in a previously unobserved fashion. Competitive processes that provide additional mechanistic insights are also described.

Original languageEnglish (US)
Pages (from-to)4425-4429
Number of pages5
JournalOrganic Letters
Volume20
Issue number15
DOIs
StatePublished - Aug 3 2018

Bibliographical note

Funding Information:
This research was supported by funding from the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R01 GM65597, then R35 GM127097) 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 (UMN) is acknowledged for performing the X-ray diffraction analyses. We thank Mr. Xiao Xiao (UMN) for assistance in collecting compound characterization data.

Funding Information:
This research was supported by funding from the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R01 GM65597, then R35 GM127097) 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 (UMN), is acknowledged for performing the X-ray diffraction analyses. We thank Mr. Xiao Xiao (UMN) for assistance in collecting compound characterization data.

Publisher Copyright:
© Copyright 2018 American Chemical Society.

Fingerprint Dive into the research topics of 'Isomerizations of Propargyl 3-Acylpropiolates via Reactive Allenes'. Together they form a unique fingerprint.

Cite this