π-Electron conjugation effects in antiaromatic dehydro[12]- and aromatic dehydro[18]-annulenes
2002
Mitzel, Frieder | Boudon, Corinne | Gisselbrecht, Jean-Paul | Gross, Maurice | Diederich, François
N,N-Dimethylanilino-substituted perethynylated dehydro[12]- and dehydro[18]-annulenes were prepared by oxidative acetylenic coupling of cis-bisdeprotected tetraethynylethene derivatives obtained by a new photochemical route; they display strongly bathochromically shifted longest-wavelength absorption bands compared to their silyl-substituted counterparts resulting from efficient intramolecular charge-transfer between the peripheral π-electron donors and the electron-accepting central acetylenic core.
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