PROMOTION OF SELECTIVITY THROUGH ORGANIZED MEDIA - FRIES REARRANGEMENT OF CALIX(N)ARENE ESTERS (N = 4,6,8)

Fries migration of various calix(n)arene esters (n = 4,6,8) under the influence of different solvents (benzene, nitrobenzene, chlorobenzene, carbon disulphide, toluene, xylene, mesitylene) and Lewis acid cataly sts (aluminium chloride, ferric chloride and boron trifluoride etherat e) has beep examined. It appears that the best conditions for the conv ersion of calix(n)arene esters to p-acyl calix(n)arenes involve the us e of aluminium chloride as the Lewis acid and carbon disulphide or ben zene as solvent. The use of toluene or mesitylene as a solvent leads t o regioselective formation of their acyl derivatives probably through the intermediacy of a host guest complex of the solvent with calix(n)a renes.