Donor-Acceptor-Acceptor 1,3-Bisdiazo Compounds: An Exploration of Synthesis and Stepwise Reactivity

Dylan J. Abrams, Huw M.L. Davies, Erik J. Sorensen

Research output: Contribution to journalArticlepeer-review

Abstract

Metal carbenes, derived from the decomposition of diazo compounds, are valued for their capacity to perform a variety of transformations. A unique class of acyclic, bis-diazo compounds, the donor-acceptor-acceptor 1,3-bisdiazo compounds, are described herein. These compounds are available from acyclic β-keto esters and especially reactive at the donor-acceptor diazo unit. These bisdiazo compounds react smoothly with rhodium acetate and alcohols to give monodiazo, cyclic orthoesters, presumably through the capture of a transient oxonium ylide.

Original languageEnglish (US)
Pages (from-to)1791-1795
Number of pages5
JournalOrganic Letters
Volume22
Issue number5
DOIs
StatePublished - Mar 6 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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