Can potassium permanganate react with trialkylboranes to form carbon-carbon bonds and boronic acids?

CHED 798

Shawn M. Maurer, Joshua T. Menig, and Clifford E. Harris. Chemistry Department, Albion College, Albion, MI 49224
A systematic study of the reactions of potassium permanganate with trialkylboranes is ongoing in our laboratory. Trialkyboranes derived from terminal and internal symmetrical alkenes were oxidized using potassium permanganate. The current procedure provides the expected alcohols and some over-oxidized product. Surprisingly, a significant amount of coupled product is formed in many cases. For example, trioctylborane is oxidized to octanol, octanal and hexadecane in a 2:1:10 ratio, respectively, in good yield. In this poster, we detail our results, propose a mechanism and begin to explore the limits of this new reaction.

 

Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster

Division of Chemical Education

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004