1-alkyl 3,5-diallyl isocyanurates as synthetic building blocks for sulfur-containing macroheterocycles.

Fattakhov, S. G.; Shulaeva, M. M.; Saifina, L. F.; Efremov, Yu. Ya.; Rizvanov, I. Kh.; Solov’eva, S. E.; Nafikova, A. A.; Azancheev, N. M.; Gubaidullin, A. T.; Litvinov, I. A.; Reznik, V. S.

2-Sulfanylethanol was added to readily available 1-alkyl 3,5-diallyl isocyanurates to obtain 1-alkyl 3,5-bis[3-(2-hydroxyethylsulfanyl)propyl] isocyanurates. Treatment of the products with thionyl chloride gave 1-alkyl 3,5-bis[3-(2-chloroethylsulfanyl)propyl] isocyanurates whose reaction with thiourea followed by hydrolysis resulted in preparation 1-alkyl 3,5-bis[3-(2-sulfanylethylsulfanyl)propyl] isocyanurates. Oxiative cyclization of the latter gave macrocyclic disulfides in 56-75% yields. The composition and structure of the macrocyclic disulfides were established on the basis of the elemental and X-ray diffraction analyses,1H and13C NMR and IR spectra, as well as MALDI-TOF and electron impact mass spectra.

SULFUR; SPECTRUM analysis; OPTICAL diffraction; HYDROLYSIS; MASS spectrometry; UREA

Russian Journal of General Chemistry, 2004, Vol 74, Issue 8, p1267

1070-3632

Academic Journal

10.1007/s11176-005-0150-0