Divergent Reactivity during the Trapping of Benzynes by Glycidol Analogs: Ring Cleavage via Pinacol-Like Rearrangements vs Oxirane Fragmentations

Juntian Zhang, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Hydroxy-containing cyclic ethers react with thermally generated benzynes to produce aryl ethers. Diverse reactivity was observed. Cleavage of the cyclic ether was involved in most of the pathways. The transformations are rationalized via initial formation of oxonium ion-containing 1,3-zwitterions arising from preferential nucleophilic attack on the benzyne by the ether oxygen. Pinacol-like rearrangements, including ring expansion, to yield aldehydes or ketones and oxirane fragmentations to generate aryl enol ethers were main competing events.

Original languageEnglish (US)
Pages (from-to)2615-2619
Number of pages5
JournalOrganic Letters
Volume21
Issue number8
DOIs
StatePublished - Apr 19 2019

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 (R35 GM127097). Some of the NMR data were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952).

PubMed: MeSH publication types

  • Journal Article
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

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