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A heavy analogue of the smallest bridgehead alkene stabilized by a base

Author

Listed:
  • Takeaki Iwamoto

    (Graduate School of Science, Tohoku University)

  • Naohiko Akasaka

    (Graduate School of Science, Tohoku University)

  • Shintaro Ishida

    (Graduate School of Science, Tohoku University)

Abstract

Bicyclo[1.1.0]but-1(2)-ene (BBE), one of the smallest bridgehead alkenes and C4H4 isomers, exists theoretically as a reactive intermediate, but has not been observed experimentally. Here we successfully synthesize the silicon analogue of BBE, tetrasilabicyclo[1.1.0]but-1(2)-ene (Si4BBE), in a base-stabilized form. The results of X-ray diffraction analysis and theoretical study indicate that Si4BBE predominantly exists as a zwitterionic structure involving a tetrasilahomocyclopropenylium cation and a silyl anion rather than a bicyclic structure with a localized highly strained double bond. The reaction of base-stabilized Si4BBE with triphenylborane affords the [2+2] cycloadduct of Si4BBE and the dimer of an isomer of Si4BBE, tetrasilabicyclo[1.1.0]butan-2-ylidene (Si4BBY). The facile isomerization between Si4BBE and Si4BBY is supported by theoretical calculations and trapping reactions. Structure and properties of a heavy analogue of the smallest bridgehead alkene are disclosed.

Suggested Citation

  • Takeaki Iwamoto & Naohiko Akasaka & Shintaro Ishida, 2014. "A heavy analogue of the smallest bridgehead alkene stabilized by a base," Nature Communications, Nature, vol. 5(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms6353
    DOI: 10.1038/ncomms6353
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