10,10 -(p-Xylylene)-bishomotriptycenes 14f～14g were prepared from bisanthrone derivatives 12f～12g. Bisanthrone derivatives were synthesized starting from anthrone through condensation, Pd/C hydrogenation and Williamson alkylation reactions. Reduction of 12f～12g by NaBH₄ in diglyme with microwave irradiation and subsequently a selective 1,7-dehydration-cyclization reaction with acid as catalyst gave bishomotriptycenes 14f～14g in quantitative yields. However, reduction of 10e, 12h and subsequently 1,4-dehydration and rearrangement reaction gave two novel bisanthracene derivatives 15i～15j instead of expected bishomotriptycenes 16i～16j. In addition, novel anthracene derivatives 11a, 13a and endoperoxides 5a～5c were also obtained as by-products.

Key words: triptycene, homotriptycene, bishomotriptycene, bisanthrone, endoperoxide, anthracene