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On the basis of an improved synthesis of the 1,3,4,5,6-pentaacetate of myo-inositol, now available in only one step from that cyclitol in yields up to 90%, we prepared various derivatives of 1-deoxy-1-mercapto-scyllo-inositol (monothioscyllitol) via the mesylate  1 a  or the trifluoromesylate  1 b ,  respectively. The non-centrosymmtric disc-shaped thioethers  3a-h  as well as their S,S-dioxides  4a-h  and the S-oxide  5f  exhibit thermotropic discotic mesophases over wide temperature ranges. The thermomesomorphism of these new sulfur compounds has been studied by optical microscopy and by differential scanning calorimetry. The pentabutyrates  3a  and  4a  as well as the dimesomorphic pentapentanoate  3 b  exhibit a probably new type of discophase D x  whereas all other monothioscyllitol derivatives with longer alkyl chains show the D ho -phase over wide temperature ranges. Of some selected new thioethers  3,  sulfones  4,  and of the sulfoxide  5f  the dipole moments have been measured which are highest with the cyano derivatives 3g and 4g at about 5 or above 6 D, respectively. These values characterize them as the strongest polar discogens studied so far.

zeitschrift für naturforschung b

Neuartige discotisch-flüssigkristalline, polare Monothioscyllitol-Derivate [1,2] / Novel Discotic Liquid Crystalline, Polar Monothioscyllitol Derivatives [1,2]