THE SYNTHESIS OF ASYMMETRIC MACROCYCLIC POLYETHERS CONTAINING NITRO GROUP ON AROMATIC RING

Article abstract of DOI:10.1016/S0040-4020(01)87410-X

The macrocyclic polyether : 12,18-dinitro-2,5,8-trioxatricyclo(14,4,0,0^9,14)eicosa-1(20),9,11,13,16,18 hexaene (6): 15,21-dinitro-2,5,8,11-tetraoxatricyclo(17,4,0,0^12,17)tricosa-1(23),12,14,16,19,21-hexaene (7) and 18,24-dinitro-2,5,8,11,14-pentaoxatricyclo)20,4,0,0^15,20)hexacosa-1(26),15,17,19,22,24-hexaene (8) have been synthesized by reaction of 2,2'-methylenebis(4-nitrophenol) (1) with diethylene glycol ditosylate (3) triethylene glycol ditosylate (4) and tetraethylene glycol ditosylate (5) respectively in the presence of KOBu-t.These compounds did not form stable complexes with alkali and alkaline-earth cations.The macrocyclic polyethers were purified by chromatoraphy and crystallization.The structure of these new compounds have been determined by elemental analysis, molecular weight determination, 1H NMR, IR and UV spectra.