N. Kuhn et al., IMIDAZOLIN-2-IMINATO DERIVATIVES OF THIOUREA .1., Zeitschrift fur Naturforschung. B, A journal of chemical sciences, 52(9), 1997, pp. 1055-1061
From 2-trimethylsilylimino-1,3-dimethylimidazoline (6, ImN-SiMe3) and
CSCl2 the imidochlorothionic acid ImN=C(S)Cl(7) is obtained; 7 gives w
ith AlCl3 the cationic isothiocyanate [ImN=C=S]AlCl4 (9). The correspo
nding imidothiourea ImN=C(S)NEt2 (12) is formed reacting Et2NC(S)Cl (1
0) and ImNLi (11). The reaction of ImN=C(S)SSiMe3 (13) with iodine giv
es the dicationic species [{ImN=C(SSiMe3)S}(2)](I-3)(2) (14) which is
transformed into the protonated imidothiourea [ImN=C(S)N(H)Im]I (16) b
y polar solvents. From 16 the imidothiourea (ImN)(2)CS (8) is obtained
as a polymeric solid. The strong pi-electron donor ability of the imi
do substituent ImN is revealed by the X-ray structure analyses of 12 a
nd 16.