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.
Bertini
V
Dipartimento di Chimica e Tecnologie Farmaceutiche ed Alimentari, Universita di Genova, Via Brigata Salerno, I-16147 Genova, Italy, and Dipartimento di Chimica e Chimica Industriale, Universita di Pisa, Via Risorgimento, 35, I-56126 Pisa, Ital.
Lucchesini
F
Pocci
M
De Munno A