T. Freund et al., BENZOYL-SUBSTITUTED TETRATHIA[1.1.1.1]METACYCLOPHANES - HIGH-YIELD SYNTHESIS, CRYSTAL-STRUCTURE, AND REDOX PROPERTIES, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (4), 1998, pp. 555-564
We report a high-yield synthesis of 3,5,17,19-tetrakis (4'-alkylbenzoy
l)-1,8,15,22-tetrathia[1.1.1.1] metacyclophanes 7([1]) via condensatio
n of dithioresorcinols 3 with benzoyl substituted meta-dichlorobenzene
s 6. The underlying reaction mechanism is discussed. The solid-state s
tructure of the macrocycle and the reduction properties of 7 have also
been investigated.