2-(Selenocyanatomethyl)-2-propenol - A convenient synthon for ligation via the deselenative allylic rearrangement of allyl selenosulfides: preparation, functional group compatibility, and application

The preparation and reactions of 2-(selenocyanatomethyl)-2-propenol are described and reveal the compatibility of the allylic selenocyanate group with a range of mild oxidizing and Lewis acidic conditions. 2-(Selenocyanatomethyl)-2-propenol and its derivatives are employed in the functionalization of simple and amino acid derived thiols in methanolic solution at room temperature to give 2-(hydroxymethyl)allyl sulfides in good to excellent yield.