Novel Silicon Substituted Dienes and their Cycloadducts

Researchers at Wake Forest University have developed novel silicon substituted dienes. These compounds have 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

  • 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

Application Fields

  • As a component for a wide variety of commercial products

Stage of Development

Various silicon-substituted dienes and their cycloadducts have been synthesized and tested (Organic Letters, 2007, 9(9), 1623-1626)

Inventors

  • Mark Welker, PhD
  • Rama Pidaparthi, PhD

Patent

U.S. Patent No. 8,110,695

Licensing Contact

Stephen J. Susalka, PhD, CLP
ssusalka@wakehealth.edu

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