Skip to content

Research at St Andrews

Unexpected α,α'-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

Research output: Contribution to journalArticle

DOI

Author(s)

Zeguo Fang, Roscoe Z. Gillatt, Alexandra M. Z. Slawin, David B. Cordes, Cameron L. Carpenter-Warren, David O'Hagan

School/Research organisations

Abstract

An unexpected and highly efficient reaction of dibenzo[a,e]cyclooctatetraene with Ag(I)F and N-bromosuccinamide in dichloromethane results in a sequential ring contraction pathway to generate bridged bicyclic α,α′-difluoroether isomers 10 and 11 where the ether oxygen is isotopically labelled from oxygen-18 water. In diethyl ether the same reaction generates the more classical vicinal difluoride isomers 13 and 14.

Close

Details

Original languageEnglish
Pages (from-to)14295-14298
Number of pages4
JournalChemical Communications
Volume55
Issue number95
Early online date5 Nov 2019
DOIs
Publication statusPublished - 11 Dec 2019

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Fluorine in pheromones: synthesis of fluorinated 12-dodecanolides as emerald ash borer pheromone mimetics

    Zhang, Q., Teschers, C. S., Callejo, R., Yang, M., Wang, M., Silk, P. J., Ryall, K., Roscoe, L. E., Cordes, D. B., Slawin, A. M. Z. & O'Hagan, D., 24 May 2019, In : Tetrahedron. 75, 21, p. 2917-2922

    Research output: Contribution to journalArticle

  2. Fluorinated cyclopropanes: Synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif

    Thomson, C., Zhang, Q., Al-Maharik, N., Buehl, M., Cordes, D. B., Slawin, A. & O'Hagan, D., 3 Jul 2018, In : Chemical Communications. In press

    Research output: Contribution to journalArticle

  3. Metabolism and hydrophilicity of the polarised ‘Janus face’ all-cis tetrafluorocyclohexyl ring, a candidate motif for drug discovery

    Rodil, A., Bosisio, S., Salah Ayoup, M., Quinn, L., Cordes, D. B., Slawin, A. M. Z., Murphy, C., Michel, J. & O'Hagan, D., 21 Mar 2018, In : Chemical Science. 9, 11, p. 3023-3028

    Research output: Contribution to journalArticle

  4. The synthesis and evaluation of fluoro-, trifluoromethyl, and iodomuscimols as GABA agonists

    Abdul Manan, M. A. F., Cordes, D., Slawin, A., Buehl, M., Liao, V., Chua, H., Chebib, M. & O'Hagan, D., 10 Aug 2017, In : Chemistry - A European Journal. 23, 45, p. 10848-10852 5 p.

    Research output: Contribution to journalArticle

Related by journal

  1. Buchwald Hartwig diversification of unprotected halotryptophans, halotryptophan containing tripeptides and the natural product barettin in aqueous conditions

    Renault, Y. J. G., Lynch, R., Marelli, E., Sharma, S. V., Pubill Ulldemolins, C., Sharp, J., Cartmell, C., Cárdenas, P. & Goss, R. J. M., 8 Oct 2019, In : Chemical Communications. Advance Article, 4 p.

    Research output: Contribution to journalReview article

  2. Continuous flow knitting of a triptycene hypercrosslinked polymer

    Lau, C. H., Lu, T., Sun, S-P., Chen, X., Carta, M. & Dawson, D. M., 28 Jul 2019, In : Chemical Communications. 55, 59, p. 8571-8574 4 p.

    Research output: Contribution to journalArticle

  3. Cu-NHC azide complex: synthesis and reactivity

    Trose, M., Nahra, F., Cordes, D. B., Slawin, A. M. Z. & Cazin, C., 14 Oct 2019, In : Chemical Communications. 55, 80, p. 12068-12071

    Research output: Contribution to journalArticle

Related by journal

  1. Chemical Communications (Journal)

    Nigel Peter Botting (Editor)
    2005 → …

    Activity: Publication peer-review and editorial work typesEditor of research journal

ID: 264360126

Top