Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones

Aimee K. Clarke, William P. Unsworth*, Richard J.K. Taylor

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The first study of the divergent reactivity of phenol/anisole-tethered donor-acceptor α-diazoketones is described. Four distinct product classes were shown to be accessible from closely related α-diazoketone precursors, with the reaction outcome dependent on the nature of the oxygen substituent on the phenol/anisole ring and the catalyst used to decompose the diazo group. Anisole and TBS-protected derivatives selectively produce three products types (cyclopropanes, tetralones and 1,2-dicarbonyls) while phenols selectively produce spirocyclic dienones.

Original languageEnglish
Early online date3 Feb 2018
Publication statusE-pub ahead of print - 3 Feb 2018

Bibliographical note

© Elsevier, 2018. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.


  • Anisole
  • Buchner reaction
  • Divergent reactivity
  • Phenol
  • α-Diazocarbonyl compounds

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