Organotin esters of dithiocarbamylacetic acids

Add time:08/02/2019    Source:sciencedirect.com

Twelve di- and tri-organotin derivatives of dithiocarbamylacetic acids of the formula RnSn(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 Mössbauer 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 revelaed by NMR (1H and 13C) spectral data. The tri-cyclohexyltin esters, however, are four-coordinate monomers in the solid state and in solution. Three distannoxanes, [(R″2SnO2CCH2S2CN-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.

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