Alkyl substituted [2.2]paracyclophane-1,9-dienes

Benjamin J. Lidster, Dharam R. Kumar, Andrew M. Spring, Chin Yang Yu, Madeleine Helliwell, James Raftery, Michael L. Turner

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

[2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.

Original languageEnglish
Pages (from-to)6079-6087
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number25
DOIs
Publication statusPublished - Jan 1 2016

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dienes
fluorides
Fluorides
preparation
benzyne
(2.2)paracyclophane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Lidster, B. J., Kumar, D. R., Spring, A. M., Yu, C. Y., Helliwell, M., Raftery, J., & Turner, M. L. (2016). Alkyl substituted [2.2]paracyclophane-1,9-dienes. Organic and Biomolecular Chemistry, 14(25), 6079-6087. https://doi.org/10.1039/c6ob00885b

Alkyl substituted [2.2]paracyclophane-1,9-dienes. / Lidster, Benjamin J.; Kumar, Dharam R.; Spring, Andrew M.; Yu, Chin Yang; Helliwell, Madeleine; Raftery, James; Turner, Michael L.

In: Organic and Biomolecular Chemistry, Vol. 14, No. 25, 01.01.2016, p. 6079-6087.

Research output: Contribution to journalArticle

Lidster, BJ, Kumar, DR, Spring, AM, Yu, CY, Helliwell, M, Raftery, J & Turner, ML 2016, 'Alkyl substituted [2.2]paracyclophane-1,9-dienes', Organic and Biomolecular Chemistry, vol. 14, no. 25, pp. 6079-6087. https://doi.org/10.1039/c6ob00885b
Lidster BJ, Kumar DR, Spring AM, Yu CY, Helliwell M, Raftery J et al. Alkyl substituted [2.2]paracyclophane-1,9-dienes. Organic and Biomolecular Chemistry. 2016 Jan 1;14(25):6079-6087. https://doi.org/10.1039/c6ob00885b
Lidster, Benjamin J. ; Kumar, Dharam R. ; Spring, Andrew M. ; Yu, Chin Yang ; Helliwell, Madeleine ; Raftery, James ; Turner, Michael L. / Alkyl substituted [2.2]paracyclophane-1,9-dienes. In: Organic and Biomolecular Chemistry. 2016 ; Vol. 14, No. 25. pp. 6079-6087.
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