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Objective:

Imagine - after a homogeneous reaction is complete, the chemist adds a catalyst or exposes the reaction mixture to soft UV light and pure product precipitates from the reaction mixture. This can be achieved with "precipitons" -- protecting groups that have controllable solubility states.

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Significance:

The precipiton strategy for chemical partitioning was developed for use in automated chemical processes and in process chemistry. In bench scale preparations the products are obtained at high purity using only 10% of the amount of solvent that would be required for isolation by extraction and chromatography. This method may be used for small or large scale reactions. We welcome partners who would like to test these ideas on the kilo scale!


 


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C &EN feature on precipitons

New->More on precipiton scavengers....

1) Precipitons as scavengers: T. Bosanac, C. S. Wilcox “A Photoactivated Precipiton for Reagent Sequestration in Solution-Phase Synthesis.” J. Amer. Chem. Soc. 2002, 124, 4194-4195.

2) M. E. Pallack, W. J. Brittain, T. Bosanac, C. S. Wilcox “Use of Precipitions for Copper Removal in Atom Transfer Radical Polymerization” Macromolecules 2002, 35, 4849-4851.

Progress:
3)
Precipitons in nitrile oxide cycloadditions: Angew. Chem. 2001, 40, 1875-1879. Full text for this article is available from Wiley-Interscience.

4) Precipitons for a-alkyl-b-ketoester synthesis: Tetrahedron Lett. 2001, 4309-4312.

5) Precipitons for Baylis-Hillman reactions: Chem. Commun. 2001, 1618-1619.

 

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