The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems

Michael J Robertson-Ralph, David C. Harrowven, Steven Gaulier, Sean Ng, Kevin I. Booker-Milburn*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

17 Citations (Scopus)

Abstract

Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused γ-lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50°C to 180°C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium-sized rings.

Original languageEnglish
Pages (from-to)1527-1531
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number5
DOIs
Publication statusPublished - 26 Jan 2015

Structured keywords

  • BCS and TECS CDTs

Keywords

  • Cyclobutenes
  • Electrocyclic reactions
  • Fused-ring systems
  • Photochemistry
  • Ring opening

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