In 1874, van 't Hoff theorized that tetravalent carbonTetravalent carbon should have bonds oriented to the corners of a tetrahedronTetrahedron. While this is generally true[1.1.1]Propellane, [1.1.1]propellanePropellane(s) provides a notable exception. The synthesis and study of this remarkable compound, with comparisons to other unusual molecules including bicyclo[1.1.0]butaneBicyclo[1.1.0]butane, will be discussed from an historical perspective.

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Exploring Variation in Bonding and Structure for Tetravalent Carbon: [1.1.1]Propellane and Inverted Carbon

  • Kathleen M. Morgan,
  • Kenneth B. Wiberg

摘要

In 1874, van 't Hoff theorized that tetravalent carbonTetravalent carbon should have bonds oriented to the corners of a tetrahedronTetrahedron. While this is generally true[1.1.1]Propellane, [1.1.1]propellanePropellane(s) provides a notable exception. The synthesis and study of this remarkable compound, with comparisons to other unusual molecules including bicyclo[1.1.0]butaneBicyclo[1.1.0]butane, will be discussed from an historical perspective.