The Synthesis, Structural Characterisation and Chemical Manipulation of the [6+3] Cycloadduct Derived from α-Tropolone O-Methyl Ether and Trimethylenemethane

Antony L. Crisp, Benjamin Noble, Brett D. Schwartz, Anthony C. Willis, Michelle L. Coote, Martin G. Banwell

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The title bicyclic system 3, the adduct arising from the formal [6+3] cycloaddition of α-tropolone O-methyl ether (1) and trimethylenemethane (2), has been prepared and subject to single-crystal X-ray analysis. The chemical manipulation of adduct 3 in a range of ways is reported, including through acid-catalysed rearrangement of the derived mono-oxide to give the bicyclo[4.3.1]undecane 21.

Original languageEnglish
Pages (from-to)1458-1467
Number of pages10
JournalAsian Journal of Organic Chemistry
Volume8
Issue number8
DOIs
Publication statusPublished - Aug 2019
Externally publishedYes

Keywords

  • oxidation
  • rearrangement
  • trimethylenemethane
  • troponoid
  • [6+3] cycloaddition

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