Novel Silicon Substituted Dienes and Their Cycloadducts (Ref # WFU 07-20)

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Novel diene compounds have many advantages over existing commercial products used in plastics, resins and glues.

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Researchers in the Department of Chemistry 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.

Competitive 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

Stage of Development

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

Application Fields

� As a component for a wide variety of commercial products

Available Materials

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

� 2,2',2"-Nitrilotris(ethanolato)(buta-1,3-dien-2-yl)silane

� Bis(1,2-benzenediolato)(1,3-butadien-2-yl)silicate

Additional Information

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

Inventors

� Dr. Mark Welker, PhD, Department of Chemistry, Wake Forest University

� Dr. Rama Pidaparthi, PhD, Department of Chemistry, Wake Forest University

Key Words

� Diene compounds

� Silicon substituted dienes