Benzodisilacyclobutadienes: 8π-Electron Systems with an Antiaromatic Silicon Ring

Shintaro Ishida, Yoshifumi Misawa, Shohei Sugawara, Takeaki Iwamoto

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Benzodisilacyclobutadienes 2 a–c were isolated as blue to green crystalline solids from the reaction of stable disilyne 1 and 1,2-dibromobenzenes in the presence of potassium graphite. In the solid state, substantial bond alternation was observed within the benzene rings of 2 a–c. In hexane, 2 a–c showed remarkable bathochromic shifts of the π→π* (HOMO→LUMO) absorption bands at 625–670 nm. NMR spectra and theoretical calculations indicated that the diamagnetic ring currents of the benzene rings of 2 a–c are considerably reduced by contributions from the antiaromatic 1,2-disilacyclobutadienes. In their entirety, the obtained results indicate that 2 a–c represent 8π-electron systems that contain an antiaromatic 1,2-disilacyclobutadiene.

Original languageEnglish
Pages (from-to)13829-13832
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number44
DOIs
Publication statusPublished - 2017 Oct 23

Keywords

  • aromaticity
  • bond alternation
  • fused-ring systems
  • multiple bonds
  • silicon

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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