IPTYCENES EXTENDED TRIPTYCENES

Article abstract of DOI:10.1016/S0040-4020(01)87581-5

Triptycene is the first member of a large scale of compounds for which we have coined the general term "iptycenes".The prefix (tri, pent, etc.) indicates the number of separated arene planes.By fusing from one to six 9,10-anthradiyl moieties on the triptycene framework, one can derive a first generation of iptycenes (Table 1).Of these, only 3, 4, 8 and a substituted 2 are known; the remainder provide a synthetic challenge.Potentially interesting practical and theorethical properties of iptycenes and particular structural features of several (i.e. 15, 16 and 24) arebriefly discussed, as are certain extensions beyond the compounds in Table 1.Methods for preparing useful synthons 35-41 are described.Three new, much improved syntheses of triptycene 29, itself a useful iptycene synthon, are presented.In addition, improved syntheses of pentiptycenes 3 and 33 are described, as well as the first syntheses of pentiptycenes 32, 34 and 52 and heptiptycene 54.The way is paved for future development of this mini-domain of unnatural products.