Synthesis of sterically rigid macrocycles by the use of pressure-induced repetitive Diels-Alder reactions.
In: Liebigs Annalen/Recueil, (1997) ; Nr. 3, S. 501-516
Zeitschriftenaufsatz / Fach: Chemie
Syn-dimethanotetrahydroanthracenes I (n = 0; R = Me, H, Ac), -tetracenes I (n = 1; R = Me, H, Ac), and -pentacene II were prepd. Highly stereoselective, pressure-induced Diels-Alder reactions of the bis-dienophiles I (n = 0-1, R = Me) with 2,3,5,6-tetramethylenebicyclo[2.2.1]heptane gave sterically rigid macrocycles III (n = 0-1, m = 0, R = MeO; n = m = 1, R = MeO, R1 = H or R = H, R1 = MeO) which have well defined cavities of different sizes.