Polystyrene Resins Containing 1,3-Propanedithiol Functions for Solid-Phase Organic Syntheses

Abstract

A completely odourless reliable synthesis of styrenic resins containing 1,3-propanedithiol functions able to form 1,3-dithiane derivatives with carbonyl compounds and back up the chemistry of thioacetals and thioketals is reported. The degree of functionalisation of the resin can be easily determined through the composition of the copolymerising mixture and confirmed by titration. The resins show good accessibility to various reagents and are effective for solid-phase synthesis being exploitable in the field of combinatorial chemistry.

Key words

solid-phase synthesis - polymeric dithiols - polymeric dithianes - umpolung reactions - ketones

References

• 1 Brown RCD. J. Chem. Soc., Perkin Trans. 1  1998,  3293 
• 2 Blackburn C. Biopolymers  1998,  47:  311 
• 3 Guillier F. Orain D. Bradley M. Chem. Rev.  2000,  100:  2091 
• 4 Lorsbach BA. Kurth MJ. Chem. Rev.  1999,  99:  1549 
• 5 Sammelson RE. Kurth MJ. Chem. Rev.  2001,  101:  137 
• 6 Bertini V. Lucchesini F. Pocci M. De Munno A. Tetrahedron Lett.  1998,  39:  9263 
• 7 Bertini V. Lucchesini F. Pocci M. De Munno A. J. Org. Chem.  2000,  65:  4839 
• 8 Gravert DJ. Janda KD. Chem. Rev.  1997,  97:  489 
• 9 Arshady R. Ledwith A. React. Polymer  1983,  1:  159 
• 10 Andrew RV. Janda KD. J. Comb. Chem.  2000,  2:  579 
• 11a The Aldrich Library of FT-IR Spectra   Vol. 2:  Pouchert CJ. Aldrich Chemical Company; USA: 1985.  p.9C 
• 11b Taber DF. Amedio JC. Yung KY. J. Org. Chem.  1987,  52:  5621 
• John Wiley MS Library, 7th Edition,
• 12a

  ID: 485116;
  

• 12b

  ID: 551046.