A novel application of tin-based alkoxide anion for deacetylation

A stannylene acetal, in the presence of CsF, is able to cleave both aromatic and aliphatic acetates rapidly and efficiently under room temperature. Control experiments indicate that both the stannylene acetal and CsF are required and play significant roles in the deacetylation process. Thus, it is likely that the tin-based alkoxide anion generated by a stannylene acetal and CsF is responsible for deacetylation.

A combination of cyclic dialkyltin alkoxide with CsF can deacetylate acetates under very mild condition, and a likely deacetylation mechanism is proposed.Figure optionsDownload as PowerPoint slide