ABSTRACT
Herein we report that readily available 4-alkenylisocouma-rins can be regarded as potent dienolate equivalents. For example, lactol silyl ethers derived from 4-alkenylisocoumarins were selectively converted to the corresponding benzo-homophthalates through a flu-oride-induced ring opening step that was followed by a ring closure through a vinylogous intramolecular aldol condensation. Likewise, nu-cleophilic activation of 4-alkenylisocoumarins directly yields diversely poly-substituted naphthalenes and anthracenes without formation of any regioisomer. Photophysical evaluation of a set of thus obtained 1,3-di- and 1,3,4-trisubstituted anthracenes reveals their distinct intra-molecular charge transfer (ICT) character during light absorption in polar solutions and excimer emission from the solid state when a face to face π-stacked molecular assembly is present in the crystal packing.
