Synthesis and physical properties of telechelic monodispersed diols 4. Monoaddition of 10‐undecenol to novel dithiols

Abstract

The synthesis of novel telechelic monodispersed diols produced from the radical monoaddition of an excess of 10-undecenol with novel a,cudithiols, initiated by peroxides, is presented. The telechelic dithiols employed were prepared from nonconjugated dienes and a commercially available dithiol, or by esterification of adipic acid with 2-mercaptoethanol. From these dithiols, the diols were selectively obtained in high yields. Such a,wdihydroxylated compounds were characterized by both 'H and l3C NMR spectroscopy. The diol which exhibits the ester functions shows excellent solubility in common organic solvents contrarily to the other ones. The physical properties (Tg, T,,, and decomposition temperatures) of these diols were compared and it is noted that the thermostability of these monodispersed telechelic diols is much better than those of the polydispersed commercially available ones such as poly(ethy1ene glyco1)s or poly(tetramethy1ene glyc0l)s. lo) or undecenic monomers 6* '') to commercially available a,u+dithiols and in every case, the yields were excellent. a) Part 3: cf. ref.*) @ 1993, Hiithig & Wepf Verlag, Base1 CCC 0025-1 16X/93/$05.00 w 0 s PI lhb. 2. 9 3