Hydrogen Migration and Lithium Iodide alfa-Elimination in 1-Iodo-1-lithioethene. Concerted vs Stepwise Mechanism

  1. Campos, P.J. 1
  2. Sampedro, D. 1
  3. Rodríguez, M.A. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Journal:
Organometallics

ISSN: 0276-7333

Year of publication: 1998

Volume: 17

Issue: 24

Pages: 5393-5396

Type: Article

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DOI: 10.1021/OM980671U SCOPUS: 2-s2.0-15444363651 WoS: WOS:000077337000029 GOOGLE SCHOLAR

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Abstract

1-Iodo-1-lithioethene is prepared from 1-iodoethene and LDA in THF. The lithiated derivative can be trapped by electrophiles, but it readily decomposes to acetylene; the decomposition process cannot be analyzed by experimental techniques. Ab initio calculations indicate that 1-iodo-1-lithioethene should be a monomer in a THF solution. Furthermore, hydrogen migration and lithium iodide α-elimination procedures should occur through a concerted mechanism. The activation barrier for the cis and trans hydrogen migration should be almost identical. © 1998 American Chemical Society.