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Hydrogenation of

van Eis MJ1, Wijsman, de Wolf WH

  • 1Scheikundig Laboratorium, Vrije Universiteit, Amsterdam, The Netherlands.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 6, 2000
PubMed
Summary
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The hydrogenation of [5]- and [6]metacyclophane rapidly produces bridgehead olefins. DFT calculations reveal that olefin 13b is hyperstable, explaining its resistance to hydrogenation.

Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • Metacyclophanes are cyclic hydrocarbons with unique structural properties.
  • Understanding the reactivity and stability of strained cyclic systems is crucial in organic chemistry.
  • Bridgehead olefins represent a challenging class of compounds due to inherent strain.

Purpose of the Study:

  • To investigate the hydrogenation pathway and thermochemistry of [5]- and [6]metacyclophane.
  • To evaluate the strain energies (SE) and olefinic strains (OS) of resulting bridgehead olefins.
  • To correlate calculated properties with experimental observations regarding olefin stability.

Main Methods:

  • Rapid hydrogenation experiments were conducted on [5]- and [6]metacyclophane.

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  • Hydrogenation enthalpies were measured experimentally.
  • Density Functional Theory (DFT) calculations were employed to assess strain energies and olefinic strains.

    • Main Results:

    • Both [5]- and [6]metacyclophane underwent rapid hydrogenation (within 10 s) yielding bridgehead olefins 13b and 12c.
    • Hydrogenation enthalpies were determined as -220 kJmol⁻¹ for 1b and -141 kJmol⁻¹ for 1c.
    • DFT calculations indicated that bridgehead olefin 13b is a hyperstable olefin, consistent with its low reactivity in hydrogenation.

    Conclusions:

    • The study elucidates the facile hydrogenation of metacyclophanes to bridgehead olefins.
    • Bridgehead olefin 13b exhibits exceptional stability, classifying it as a hyperstable olefin.
    • Experimental and computational data provide insights into the relationship between strain, stability, and reactivity in cyclic olefins.