Organotin esters of dithiocarbamylacetic acids

Article abstract of DOI:10.1016/0022-328X(91)86139-H

Twelve di- and tri-organotin derivatives of dithiocarbamylacetic acids of the formula R_nSn(O2CCH2S2CNR'2)_4-n (R = Me, ⁿBu, ^cHex, Ph; NR'2 = NMe2, NEt2, N(CH2)4, N(CH2CH2)2O; n = 3, 2) have been prepared.On the basis of IR and Moessbauer spectroscopic data, the trimethyl-, tri-n-butyl- and triphenyltin derivatives are assigned a carboxylate-bridged structure with trans-C3SnO2 trigonal bipyramidal geometry at tin.The diorganotin dithiocarbamylacetates also adopt a bridged structure with a trans-C2SnO4 octahedral geometry at tin.The triorganotin esters dissociate into four-coordinate species in solution, as revealed by NMR (1H and 13C) spectral data.The tri-cyclohexyltin ester, however, are four-coordinate monomers in the solid state and in solution.Three distannoxanes, <(R''2SnO2CCH2SnCN-Me2)O2>2 (R''2Sn = Bu2Sn, BuPhSn, Ph2Sn), were obtained as adventituous products during attempts to make the diorganotin esters from the diorganotin dihalides; for these distannoxanes the spectral data are interpreted in terms of skew-trapezoidal bipyramidal coordination at the tin atoms.