Akira Matsuura

Synthesis and electronic properties of anthracene fully annelated with bicyclo[2.2.2]octene frameworks

Anthracene derivative 4 annelated with four bicyclo[2.2.2]octene (BCO) units was newly synthesized by the Diels-Alder reaction of BCO dimer with p -benzoquinone as a key reaction, and its electronic properties were investigated. The remarkable effect of BCO annelation was observed in its redox behavior, and 4 was readily transformed into stable cation radical 4 +• and dication 4 2+ .

Reactions of a novel benzyne annelated with two bicyclo[2.2.2]octene units

Anthranilic acid 9 and o-dibromobenzene 14 annelated with two bicyclo[2.2.2]octene units were synthesized as the precursors for titled benzyne 3. The generation of 3 was confirmed by trapping with furan and its derivative. In the absence of trapping agent, benzyne 3 generated by diazotization of 9 gave acridone 12 while that generated via lithiation of 14 dimerized to give BCO-annelated biphenylene 11. The HOMO level of 11 is considerably raised as shown by cyclic voltammetry.

Synthesis, structure and properties of naphthalene fully annelated with bicyclo[2.2.2]octene frameworks

Novel naphthalene derivative 4 annelated with four bicyclo[2.2.2]octene frameworks was synthesized. X-ray analysis showed that the acene core of 4 deviates from planarity. The remarkable effect of annelation was observed in its oxidizability as revealed by cyclic voltammetry, and 4 was readily converted to highly stable radical cation 4 +• and to the dication 4 2+ .

Monooxygen transfer potential of the transannular ozonide of 9-tert-butyl-10-methylanthracene

Abstract The efficiency of oxygen transfer from the transannular ozonide 1 to several organic substrates was investigated. The efficiency was estimated to be as high as 90% in the case of Ph 3 P as the substrate.