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C4-aldehyde of guaiazulene: synthesis and derivatisation

Organic and Biomolecular Chemistry, 2021-03, Vol.19 (11), p.2502-2511 [Peer Reviewed Journal]

Publisher Copyright: © The Royal Society of Chemistry 2021. Copyright: Copyright 2021 Elsevier B.V., All rights reserved. ;ISSN: 1477-0520 ;ISSN: 1477-0539 ;EISSN: 1477-0539 ;DOI: 10.1039/d0ob02567d ;PMID: 33661271

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  • Title:
    C4-aldehyde of guaiazulene: synthesis and derivatisation
  • Author: Williams, Georgia E. ; Kociok-Köhn, Gabriele ; James, Tony D.
  • Subjects: Organic Chemistry
  • Is Part Of: Organic and Biomolecular Chemistry, 2021-03, Vol.19 (11), p.2502-2511
  • Description: Guaiazulene is an alkyl-substituted azulene available from natural sources and is a much lower cost starting material for the synthesis of azulene derivatives than azulene itself. Here we report an approach for the selective functionalisation of guaiazulene which takes advantage of the acidity of the protons on the guaiazulene C4 methyl group. The aldehyde produced by this approach constitutes a building block for the construction of azulenes substituted on the seven-membered ring. Derivatives of this aldehyde synthesised by alkenylation, reduction and condensation are reported, and the halochromic properties of a subset of these derivatives have been studied.
  • Language: English
  • Identifier: ISSN: 1477-0520
    ISSN: 1477-0539
    EISSN: 1477-0539
    DOI: 10.1039/d0ob02567d
    PMID: 33661271
  • Source: Opus: University of Bath's Eprints IR
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