3 years ago

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

Benzodisilacyclobutadienes: 8π-Electron Systems with an Antiaromatic Silicon Ring
Yoshifumi Misawa, Shohei Sugawara, Takeaki Iwamoto, Shintaro Ishida
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 ππ* (HOMOLUMO) 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. Slowing the flow: Benzodisilacyclobutadienes (see structure) were synthesized and isolated as blue and green crystalline solids. According to their solid-state structures, UV/Vis absorption and NMR spectra, and theoretical calculations, these benzodisilacyclobutadienes exist as 8π-electron systems that contain an antiaromatic 1,2-disilacyclobutadiene.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707553

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