One-step synthesis of pentavalent triphenylantimony derivatives Ph3Sb(OSiR3)2, Ph3Sb(OCH2CH2)2NH and Ph3Sb(OCH2CH2NMe2)2: X-ray molecular structure of Ph3Sb(OSiMe3)2

Pentavalent bis(triorganosiloxy)triphenylantimony derivatives, Ph3Sb(OSiR3)2 (R = Me, Ph), were synthesized by reaction of triphenylantimony with trimethyl- or triphenylsilanol in the presence of tert-butylhydroperoxide by the mild reaction conditions (0–5 °C, 2 h). The reaction of triphenylantimony with diethanolamine in the presence of tert-butylhydroperoxide gave the cyclic compound Ph3Sb(OCH2CH2)2NH. The mixture of Ph3SbO and Ph3Sb(OCH2CH2NMe2)2 was obtained by the reaction of triphenylantimony with 2-(N,N-dimethylamino)ethanol in the presence of tert-butylhydroperoxide.

Graphical abstractThe simplicity of the procedure and mildness of the reaction conditions (0–20 °C, 2–24h) are the main advantages of this method. Ph3Sb(OSiR3)2 (R = Me (1), Ph (2)) and Ph3Sb(OCH2CH2)2NH (3) are stable to air and moisture resistant. The mixture of Ph3Sb(OCH2CH2NMe2)2 (4) with Ph3SbO was obtained. 4 formed very rapidly. Then it is hydrolyzed to Ph3SbO.Figure optionsDownload full-size imageDownload as PowerPoint slide