SYNTHESIS AND STRUCTURE OF CHIRAL DIAZACORONANDS DERIVED FROM L-TARTARIC ACID

Six chiral di-N-p-toluenesulphonyl diazacoronands derived from L-tarta ric acid were synthesized by the modified Richman Atkins procedure, Th e deprotection of isopropylidene acetal led to the formation of compou nds 7 possessing an 1,2-diol subunit. H-1 and C-13 NMR, UV and MS tech niques were used for structure assignment, The determination of the X- ray structure of compounds 6a and 7b pointed to a variety of ring conf ormations, The shape of the molecules is to a great extent determined by a system of intra- and intermolecular hydrogen bonds of a O...O and C...O nature, Compound 7b was found to form a supramolecular assembly (H-bonded dimers) both in solution and in solid state, Complexation s tudies of this group of compounds suggest that this process is mediate d by the hydroxyl and sulfonyl group oxygen atoms.