Novel Silicon Substituted Dienes and their Cycloadducts

Researchers at Wake Forest University have developed novel silicon substituted dienes, compounds with potential applications as cross-linking agents for silicone polymers as well as adhesion promoters for polyamine and epoxy resins. These types of compounds can also be used to make sol-gels and as precursors for the formation of thin solid films.

These compounds are useful components for a number of commercial products, including:

  • Silicon-containing polyester resins
  • Polyamide resins
  • Silane coupling agents
  • Plasticizers for vinyl chloride
  • Curing agents for epoxy resins
  • Pharmaceuticals and agricultural products

Unlike existing silicon substituted dienes, these novel compounds are produced in high yield, enhance exo-selectivity in Diels-Alder cycloaddition reactions, and are significantly more stable than other highly reactive silicon dienes such as “Danishefsky’s diene.” Furthermore, these new reagents exist as solids at room temperature, which confers additional advantages in terms of purification and ease of use.

Benefits of the Novel Silicon Substituted Dienes

  • Produced in high yield
  • Enhance exo-selectivity in Diels-Alder cycloaddition reactions
  • More stable than other highly reactive silicon dienes such as “Danishefsky’s diene”
  • Exist as solids at room temperature, which confers additional advantage in purification and ease of use

Status

  • Various silicon-substituted dienes and their cycloadducts have been synthesized and tested (Organic Letters, 2007, 9(9), 1623-1626)
  • Issued U.S. Patent 8,110,695

Available Materials

Samples of the following silicon substituted dienes are available for research purposes from Strem Chemicals:

Additional Information

Organic Letters, 2007, 9(9), 1623-1626

Inventors

Mark Welker, PhD, Department of Chemistry
Rama Pidaparthi, PhD, Department of Chemistry

Licensing Contact

Stephen Susalka, PhD, CLP
Associate Director, Commercialization
+1.336.716.4029
ssusalka@wakehealth.edu

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