Preparation, spectroscopic studies and structure of bis(triorganostannyl) esters of substituted aliphatic dicarboxylic acids

Add time:07/16/2019    Source:sciencedirect.com

Bis(triorganostannyl) esters of phenylmaleic acid, citraconic acid, maleic acid, phenylsuccinic acid, methylsuccinic acid and succinic acid, R3SnO2CCR1: CHCO2SnR3 (R  Bu, Ph, Cy; R1  Ph, Me, H) and R3SnO2CCHR1·CH2CO2SnR3 (R  Bu, Ph; R1  Ph and R  Bu, Ph, Cy; R1  Me, H), have been prepared from R3SnOH or (BU3Sn)2O and the dicarboxylic acid or its anhydride. The structures of these compounds in the solid state are discussed with reference to their IR and Mössbauer spectra. The crystal structures of the bis(triphenylstannyl) esters of phenylmaleic acid and citraconic acid have been determined by single crystal X-ray diffraction. In the first diester, both tin atoms are occupying tetrahedral geometries, with no short intermolecular O ⋯ Sn contacts. In bis(triphenyltin) citraconate, the carboxylatotin attached to the substituted olefinic carbon is also four coordinate, but the second tin atom is five coordinate, due to intermolecular coordination by a carboxylate group from a neighbouring molecule [Sn ⋯ O 2.397(3) Å], thereby giving rise to a polymeric chain structure. The tributylstannyl monoester of citraconic acid has been synthesized and its structure in solution assigned by 13C and 119Sn NMR spectroscopy and, in the solid state, by IR and Mössbauer spectroscopy.

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