REDUCTION OF DMAD-ANTHRACENE ADDUCTS - SYNTHESIS AND CONFORMATIONS OF SUBSTITUTED CYCLODECADIENES

A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.