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On the Prins reaction of terminal olefins and formaldehyde in trifluoroacetic acid

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Chemistry of Heterocyclic Compounds Aims and scope

A Correction to this article was published on 01 June 2018

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The Prins reaction of 1-heptene, as a representative terminal alkene, with formaldehyde in trifluoroacetic acid produces 3-butyl-4-(trifluoroacetoxy)tetrahydropyran and/or 3-butyl-4-hydroxytetrahydropyran; it does not provide (as previously reported by Talipov and coworkers) a route to 3-alkyl-2,5-dihydrofurans and 4-alkyl-3-hydroxytetrahydrofurans.

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Change history

  • 04 August 2018

    On p. 476, the high-resolution mass spectrum of compound trans-4b should be read as "Found, m/z: 141.1272 [M–OCOCF3]+. C9H17O. Calculated, m/z: 141.1274".

Notes

  1. E-mail from Prof. R. F. Talipov, 13th February 2008.

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The authors thank the Higher Committee for Education Development in Iraq for studentship support (to H.A.A.A.), the EPSRC and Roche for a CASE award (to M.A.H.S.), and Prof. Talipov (Bashkir State University) for useful correspondence.

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Authors and Affiliations

  1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK

    Hasanain A. A. Almohseni, Matthew A. H. Stent & David M. Hodgson

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  1. Hasanain A. A. Almohseni
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  2. Matthew A. H. Stent
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  3. David M. Hodgson
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Correspondence to David M. Hodgson.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 474–477

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Almohseni, H.A.A., Stent, M.A.H. & Hodgson, D.M. On the Prins reaction of terminal olefins and formaldehyde in trifluoroacetic acid. Chem Heterocycl Comp 54, 474–477 (2018). https://doi.org/10.1007/s10593-018-2293-z

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