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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 6
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Original Articles

Facile Method for Solid‐Phase Synthesis of Vinyl Sulfones Using Polystyrene‐Supported Selenomethyl Aryl Sulfone

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Pages 815-821 | Received 18 Feb 2004, Published online: 20 Aug 2006

References

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