Nucleophilic substitution in vinylic halides


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ABSTRACT NUCLEOPHILIC substitution of a halogen atom directly attached to a double bond, as in the vinyl and phenyl halides, does not readily take place1–3. Nevertheless, cases of


substitution in vinylic halides are recorded in the literature4, and facile substitution has been reported for compounds containing electron-withdrawing substituents in the β-position with


respect to the halogen5. An obvious analogy exists with aromatic systems in which, as has been demonstrated by numerous experiments, nucleophilic substitution occurs readily only when


electron-withdrawing groups are present at suitable positions in the ring. Access through your institution Buy or subscribe This is a preview of subscription content, access via your


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* Learn about institutional subscriptions * Read our FAQs * Contact customer support SIMILAR CONTENT BEING VIEWED BY OTHERS ANTI-MARKOVNIKOV HYDRO(AMINO)ALKYLATION OF VINYLARENES VIA


PHOTOREDOX CATALYSIS Article Open access 12 October 2021 ASYMMETRIC Α-C(_SP_3)−H ALLYLIC ALKYLATION OF PRIMARY ALKYLAMINES BY SYNERGISTIC IR/KETONE CATALYSIS Article Open access 31 January


2024 CATALYTIC ASYMMETRIC ADDITION OF AN AMINE N–H BOND ACROSS INTERNAL ALKENES Article 03 November 2020 REFERENCES * Hughes, _Trans. Farad. Soc._, 37, 603 (1941). Article  CAS  Google


Scholar  * Bunnett, _Chem. Revs._, 49, 273 (1951). Article  CAS  Google Scholar  * Gold, _J. Chem. Soc._, 1431 (1951). * Lovenich, Losen and Dierichs, _Ber._, 60, 950 (1927). Google Scholar


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AFFILIATIONS * William Ramsay and Ralph Forster Laboratories, University College, Gower Street, London, W.C.1 D. EMYR JONES & C. A. VERNON Authors * D. EMYR JONES View author


publications You can also search for this author inPubMed Google Scholar * C. A. VERNON View author publications You can also search for this author inPubMed Google Scholar RIGHTS AND


PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE JONES, D., VERNON, C. Nucleophilic Substitution in Vinylic Halides. _Nature_ 176, 791–792 (1955).


https://doi.org/10.1038/176791a0 Download citation * Issue Date: 22 October 1955 * DOI: https://doi.org/10.1038/176791a0 SHARE THIS ARTICLE Anyone you share the following link with will be


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