Bismuth compounds in organic synthesis: Bismuth bromide catalyzed addition of allylsilanes to conjugated enones

CHED 217

Christopher M. Duncan, Laboratory for Environment Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, 201 East Beecher Street, Bloomington, IL 61701 and Ram S. Mohan, rmohan@iwu.edu, Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, 201 East Beecher Street, Bloomington, IL 61701.
The conjugate addition of allyltrimethylsilanes to enones catalyzed by titanium tetrachloride is a useful method to form carbon-carbon bonds. However, the use of stoichiometric amounts of titanium tetrachloride, which is corrosive and difficult to handle, makes this procedure less attractive. We report that bismuth bromide in the presence of trimethylsilylchloride efficiently catalyzes the conjugate addition of allyltrimethylsilane to enones. Bismuth compounds are attractive because they are remarkably low in toxicity and easy to handle. The results of this study will be presented.

 

Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Chemical Education

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005