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Efforts toward distorted spiropentanes.

Kuan-Jen Su1, Jean-Luc Mieusset, Vladimir B Arion

  • 1Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, Austria.

The Journal of Organic Chemistry
|October 14, 2010
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Summary
This summary is machine-generated.

Tetravinylbenzene was synthesized efficiently using Suzuki-Miyaura coupling. Cyclopropanation reactions yielded highly distorted spiropentanes, with stability analyzed by DFT calculations.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Tetravinylbenzene is a useful building block in organic synthesis.
  • Previous methods for tetravinylbenzene synthesis were less efficient.

Purpose of the Study:

  • To develop an improved synthesis of tetravinylbenzene.
  • To explore the synthesis and properties of novel spiropentane derivatives.

Main Methods:

  • Suzuki-Miyaura cross-coupling reaction for tetravinylbenzene synthesis.
  • Intermolecular and intramolecular cyclopropanation reactions.
  • Density Functional Theory (DFT) calculations for stability analysis.

Main Results:

  • Tetravinylbenzene synthesized in nearly quantitative yield via a one-step Suzuki-Miyaura coupling.
  • Formation of gem-dibromide adducts through intermolecular cyclopropanation.
  • Synthesis of a highly distorted spiropentane (compound 11) with a C-C-C bond angle of 163.5° via intramolecular cyclopropanation.

Conclusions:

  • The improved Suzuki-Miyaura coupling offers a highly efficient route to tetravinylbenzene.
  • Novel, highly strained spiropentane structures can be accessed through cyclopropanation strategies.
  • DFT calculations provide insights into the stability of these unique strained molecules.