Polymeric Reagents with Propane-1,3-dithiol Functions and Their Precursors for Supported Organic Syntheses

Reliable completely odorless syntheses of soluble copolymeric reagents of styrene type containing propane-1,3-dithiol functions able to convert carbonyl compounds into 1,3-dithiane derivatives and to support other useful transformations are reported together with their progenitor copolymers containing benzenesulfonate or thioacetate groups perfectly stable in open air and suitable for unlimited storage. The effectiveness of the prepared reagents as tools for polymer-supported syntheses to produce ketones by aldehyde umpolung and alkylation is tested in the conversion of benzaldehyde to phenyl n-hexyl ketone starting from copolymers with different contents of active units and molecular weights. To facilitate the adaptation of the prepared soluble copolymeric reagents to other possible applications, a table of solvents and nonsolvents is presented.