RESUMEN
Naphthodislacyclobutadiene 3 and anthradisilacyclobutadiene 4 were synthesized and characterized. In these compounds, the diatropic ring current on the benzene ring adjacent to the disilacyclobutadiene moiety decreases while that on the other benzene rings remains intact. The longest-wavelength absorption bands of 3 and 4 were hypsochromically shifted compared to those of benzodisilacyclobutadiene 1a despite the extended π-electron systems.
RESUMEN
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 πâπ* (HOMOâLUMO) absorption bands at 625-670â 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.